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CAS 97-72-3

2-Methylpropanoyl 2-methylpropanoate2-Methylpropionic anhydrideIsobutyric anhydrideDimethylacetic anhydridealpha-Methylpropionic anhydrideisobutyric anhydride

Codes: (VIb)1140100-1-a, (IV)1140100-2-a, (IIa)1140100-3-a, Molnupiravir-003, CICL-002

Application context (from source-drug indications)

COVID-19Deuremidevir hydrobromide呼吸道合胞体病毒感染Deuremidevir hydrobromide亨尼波病毒属感染Deuremidevir hydrobromideCOVID-19Molnupiravir呼吸道合胞体病毒感染MolnupiravirInfluenza virus infectionMolnupiravirRenal impairmentMolnupiravirHepatic function declineMolnupiravirAsthmaCiclesonidePerennial allergic rhinitisCiclesonideSeasonal allergic rhinitisCiclesonideAllergic rhinitisCiclesonide支气管肺发育不良CiclesonideCOVID-19Ciclesonide

Source drugs (routes using this intermediate)

DrugTierExpiry
Deuremidevir hydrobromideTier C — Watch / trade-
MolnupiravirTier B — Position early-
CiclesonideTier C — Watch / trade-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

Deuremidevir hydrobromideOptimised routesteps: 7total yield: /
(2R,3R,4R,5R)-2-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile→(2R,3R,4R,5R)-2-(4-Amino-5-iodopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]oxolane-2-carbonitrile→(2R,3R,4R,5R)-2-[4-Amino-5-deuteropyrrolo[2,1-f][1,2,4]triazin-7-yl]-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]oxolane-2-carbonitrile→(2R,3R,4S,5R)-2-(4-Amino-5-deuteriopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile→N'-[7-[(2R,3R,4S,5R)-2-Cyano-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-deuteropyrrolo[2,1-f][1,2,4]triazin-4-yl]-N,N-dimethylmethanimidamide→2-Methylpropanoyl chloride→2-Methylpropanoyl 2-methylpropanoate→(2R,3R,4R,5R)-2-Cyano-2-[4-[(Z)-[(dimethylamino)methylidene]amino]-5-deuteropyrrolo[2,1-f][1,2,4]triazin-7-yl]-5-[[(2-methylpropanoyl)oxy]methyl]oxolane-3,4-diyl bis(2-methylpropanoate)→(2R,3R,4R,5R)-2-[4-Amino-5-deuteropyrrolo[2,1-f][1,2,4]triazin-7-yl]-2-cyano-5-[[(2-methylpropanoyl)oxy]methyl]oxolane-3,4-diyl bis(2-methylpropanoate)
Deuremidevir hydrobromideOptimised routesteps: 4total yield: /
(2R,3R,4R,5R)-2-(4-Amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]oxolane-2-carbonitrile→(2R,3R,4R,5R)-2-(4-Amino-5-iodopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]oxolane-2-carbonitrile→(2R,3R,4R,5R)-2-(4-Amino-5-chloropyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]oxolane-2-carbonitrile→(2R,3R,4S,5R)-2-(4-Amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile→(2R,3R,4S,5R)-2-(4-Amino-5-iodopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile→(2R,3R,4S,5R)-2-(4-Amino-5-chloropyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile→(2R,3R,4S,5R)-2-(4-Amino-5-deuteriopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile→2-Methylpropanoyl 2-methylpropanoate→(2R,3R,4R,5R)-2-[4-Amino-5-deuteropyrrolo[2,1-f][1,2,4]triazin-7-yl]-2-cyano-5-[[(2-methylpropanoyl)oxy]methyl]oxolane-3,4-diyl bis(2-methylpropanoate)→(2R,3R,4R,5R)-2-(4-Amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-cyano-5-[[(2-methylpropanoyl)oxy]methyl]oxolane-3,4-diyl bis(2-methylpropanoate)→(2R,3R,4R,5R)-2-(4-Amino-5-iodopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-cyano-5-[[(2-methylpropanoyl)oxy]methyl]oxolane-3,4-diyl bis(2-methylpropanoate)→(2R,3R,4R,5R)-2-(4-Amino-5-chloropyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-cyano-5-[[(2-methylpropanoyl)oxy]methyl]oxolane-3,4-diyl bis(2-methylpropanoate)→(2{R},3{R},4{S},5{R})-2-(4-Azanylpyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolane-2-carbonitrile→((2R,3R,4R,5R)-5-(4-Aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-5-cyano-3,4-bis(2-methylpropanoyloxy)tetrahydrofuran-2-yl)methyl 2-methylpropanoate
Deuremidevir hydrobromideOptimised routesteps: 3total yield: /
(2R,3R,4S,5R)-2-(4-Amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile→(2R,3R,4S,5R)-2-(4-Amino-5-deuteriopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile→(2R,3R,4S,5R)-2-[4-Amino-5-deuteropyrrolo[2,1-f][1,2,4]triazin-7-yl]-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile hydrogen chloride→2-Methylpropanoyl 2-methylpropanoate→2-Methylpropanoyl chloride→(2R,3R,4R,5R)-2-[5-Bromo-4-(2-methylpropanamido)pyrrolo[2,1-f][1,2,4]triazin-7-yl]-2-cyano-5-[[(2-methylpropanoyl)oxy]methyl]oxolane-3,4-diyl bis(2-methylpropanoate)→(2R,3R,4R,5R)-2-Cyano-2-[4-(2-methylpropanamido)-5-deuteropyrrolo[2,1-f][1,2,4]triazin-7-yl]-5-[[(2-methylpropanoyl)oxy]methyl]oxolane-3,4-diyl bis(2-methylpropanoate)
MolnupiravirOriginator routesteps: 10total yield: /
MolnupiravirOptimised routesteps: 12total yield: /
Molnupiravir-012→Methyl 2,3-O-isopropylidene-beta-D-ribofuranoside→Methyl 5-O-benzoyl-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside→1,2,3-Tri-O-acetyl-5-O-benzoyl-beta-D-ribofuranose→2-Methylpropionyl chloride→N-(2-Oxo-1,2-dihydropyrimidin-4-yl)acetamide→N-Acetyl-2',3'-di-O-acetyl-5'-O-benzoylcytidine→Cytosine-1-beta-D-ribofuranoside→Sulfuric acid 2',3'-O-(1-methylethylidene)cytidine→2',3'-O-(1-Methylethylidene)cytidine→2',3'-O-(1-Methylethylidene)-N-(2-methylpropanoyl)-5'-O-(2-methylpropanoyl)cytidine→Hydroxylamine→Hydroxylamine hydrochloride→Hydroxylamine sulfate→N-Hydroxy-2',3'-O-(1-methylethylidene)-5'-O-(2-methylpropanoyl)cytidine→2-Methylpropionic anhydride
MolnupiravirOptimised routesteps: 11total yield: /
MolnupiravirOptimised routesteps: 6total yield: 5.14g(Molnupiravir)
N-[(Dimethylamino)methylidene]cytidine→5'-O-(2-Methylpropanoyl)cytidine oxalate→N,O2',O3'-Tris[(dimethylamino)methylidene]cytidine→1-(beta-D-Ribofuranosyl)cytosine→Acetone O-isobutyryloxime→Isobutyryl chloride→2-Methylpropionic acid→5'-O-Isobutyryl cytidine→Dimethylacetic anhydride
MolnupiravirOptimised routesteps: 2total yield: 147g(Molnupiravir)
5’-Isobutyryluridine→Uracil-1-beta-D-ribofuranoside→Dimethylacetic anhydride
MolnupiravirOptimised routesteps: 3total yield: /
5-O-(2-Methylpropanoyl)-D-ribofuranose→Molnupiravir-012→alpha-Methylpropionic anhydride→2,4-Dihydroxypyrimidine→5'-O-(2-Methylpropanoyl)uridine
MolnupiravirOptimised routesteps: 7total yield: 343mg(Molnupiravir)
N-[(Dimethylamino)methylidene]-2',3'-O-[(dimethylamino)methylidene]-5'-O-(2-methylpropanoyl)cytidine→N-[(Dimethylamino)methylidene]-5'-O-(2-methylpropanoyl)cytidine→N-[(Hydroxyimino)methyl]-5'-O-(2-methylpropanoyl)cytidine→Cytosine beta-D-riboside→N,O2',O3'-Tris[(dimethylamino)methylidene]cytidine→Dimethylacetic anhydride
MolnupiravirOptimised routesteps: 4total yield: 42.9g(Molnupiravir)
2',3'-O-[(Dimethylamino)methylidene]-N-hydroxycytidine→2',3'-O-[(Dimethylamino)methylidene]-N-hydroxy-5'-O-(2-methylpropanoyl)cytidine→Cytosine-1-beta-D-ribofuranoside→N4-Hydroxycytidine→Isobutyric anhydride
MolnupiravirOptimised routesteps: 3total yield: /
2',3'-O-(1-Methylethylidene)-5'-O-(2-methylpropanoyl)-N-[(2-methylpropanoyl)oxy]cytidine→5'-O-(2-Methylpropanoyl)-N-[(2-methylpropanoyl)oxy]cytidine→N-Hydroxy-2',3'-O-(1-methylethylidene)cytidine→alpha-Methylpropionic anhydride
MolnupiravirOptimised routesteps: 7total yield: 1.65g(Molnupiravir)
1,2,3-Tri-O-acetyl-5-O-(triphenylmethyl)-D-ribofuranose→2',3'-Di-O-acetyluridine→2',3'-Di-O-acetyl-5'-O-(2-methylpropanoyl)uridine→1-[2,3-Di-O-acetyl-5-O-(2-methylpropanoyl)-beta-D-ribofuranosyl]-4-[[2,4,6-tri(propan-2-yl)benzene-1-sulfonyl]oxy]pyrimidin-2(1H)-one→Molnupiravir-052→2,4(1H,3H)-Pyrimidinedione→2-Methylpropionic anhydride→Hydroxylamine hydrochloride
MolnupiravirOptimised routesteps: 4total yield: /
Sulfuric acid 2',3'-O-benzylidenecytidine (1/1)→Sulfuric acid 2',3'-O-methylidenecytidine (1/1)→2',3'-O-Benzylidene-5'-O-(2-methylpropanoyl)cytidine→2',3'-O-Methylidene-5'-O-(2-methylpropanoyl)cytidine→2',3'-O-Benzylidene-N-hydroxy-5'-O-(2-methylpropanoyl)cytidine→N-Hydroxy-2',3'-O-methylidene-5'-O-(2-methylpropanoyl)cytidine→1-(beta-D-Ribofuranosyl)cytosine→2-Methylpropionic anhydride→Hydroxylamine sulfate
MolnupiravirOptimised routesteps: 5total yield: 4.15g(Molnupiravir)
1-[2,3-O-(1-Methylethylidene)-5-O-(2-methylpropanoyl)-beta-D-ribofuranosyl]-4-sulfanylidene-3,4-dihydropyrimidin-2(1H)-one→1-(beta-D-Ribofuranosyl)uracil→1-[(3aR,4R,6R,6aR)-6-(Hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione<-fgf->2',3'-O-Isopropylideneuridine→2-Methylpropionic anhydride→2',3'-O-(1-Methylethylidene)-5'-O-(2-methylpropanoyl)uridine→Hydroxylamine→N-Hydroxy-2',3'-O-(1-methylethylidene)-5'-O-(2-methylpropanoyl)cytidine
MolnupiravirOptimised routesteps: 10total yield: /
2(S)-(1,1,1-Triphenylmethoxymethyl)oxirane→(Vinyl)magnesium bromide→(2S)-1-(Triphenylmethoxy)pent-4-en-2-ol→(3S)-3-[[tert-Butyl(diphenyl)silyl]oxy]-4-(triphenylmethoxy)butanal→(2S,3aS,9aR)-2-[(Triphenylmethoxy)methyl]-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-one→Iodoform→tert-Butyl[[(2S,4E)-5-iodo-1-(triphenylmethoxy)pent-4-en-2-yl]oxy]diphenylsilane→1-[(1E,4S)-4-Hydroxy-5-(triphenylmethoxy)pent-1-en-1-yl]pyrimidine-2,4(1H,3H)-dione→1-[(2R,5S)-5-(Trityloxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione→[(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl 2-methylpropanoate→2,4(1H,3H)-Pyrimidinedione→2-Methylpropionic anhydride→5'-O-(2-Methylpropanoyl)uridine→Hydroxylamine sulfate
MolnupiravirOptimised routesteps: 6total yield: 85mg(Molnupiravir)
1-(beta-D-Ribofuranosyl)cytosine<-fgf->→N4-Hydroxycytidine→Isobutyric anhydride→5'-O-(2-Methylpropanoyl)-N-[(2-methylpropanoyl)oxy]cytidine→N-[(2-Methylpropanoyl)oxy]cytidine

Intermediates available on this site

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SupplierProductPrice bandMOQLead timeQualificationsAction
Unibest Taizhou GMP-like Site((3aR,4R,6R,6aR)-6-(4-(hydroxyamino)-2-oxopyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl isobutyrate
Pharmaceutical Intermediates
On requestOn requestOn request
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