133697-35-5

Basic information

• Product Name: {(2S,5R)-5-[5-(hydroxymethyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-2-yl}methyl 4-methylbenzoate
• CAS NO: 133697-35-5
• Molecular Formula: C₁₈H₂₀N₂O₆
• Molecular Weight: 360.3612
• Mol File: 133697-35-5.mol

Chemical Properties

• Density: 1.337g/cm³
• Refractive Index: 1.585
• CAS DataBase Reference: {(2S,5R)-5-[5-(hydroxymethyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-2-yl}methyl 4-methylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: {(2S,5R)-5-[5-(hydroxymethyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-2-yl}methyl 4-methylbenzoate(133697-35-5)
• EPA Substance Registry System: {(2S,5R)-5-[5-(hydroxymethyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-2-yl}methyl 4-methylbenzoate(133697-35-5)

Safety Data

• Hazardous Substances Data: 133697-35-5(Hazardous Substances Data)

Upstream product

• 133635-44-6 methyl 2,3-dideoxy-5-O-(4-methylbenzoyl)-D-glycero-pentofuranoside 
• 111878-20-7 (2,4-Bis-trimethylsilanyloxy-pyrimidin-5-yl)-methanol 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 133635-43-5 (S)-γ-(4-methylbenzoyloxymethyl)-γ-butyrolactone 
• 874-60-2 4-methyl-benzoyl chloride 

Relevant articles and documents

Synthesis of 2',3'-Dideoxynucleosides from 5-Alkoxymethyluracils

A modified synthesis of protected 2,3-dideoxyribose 5 starting from L-glutamic acid (1) is described.Reaction of 5 with silylated 5-hydroxymethyluracil 7a and 5-alkoxymethyluracils 7b-e in the presence of trimethylsilyl triflate afforded an anomeric mixture of 2',3'-dideoxyuridine derivatives 8a-e and 9a-e.Deprotection with methanolic ammonia and separation by chromatography gave the corresponding nucleosides 10a-e and 11a-e.Treatment of 9b-e with tri(1H-1,2,4-triazol-1-yl)phosphine oxide and subsequent reaction of 12b-e with ammonia in dioxane afforded the cytosine derivatives 13b-e which on treatment with methanolic ammonia gave the corresponding 2',3'-dideoxycytidine derivatives 14b-e and 15b-e.In contrast with the parent compounds, these alkoxymethyl derivatives had no appreciable activity against human immunodeficiency virus (HIV-1).