68045-07-8

Basic information

• Product Name: 1,3,5-Tri-O-benzoyl-2-O-methyl-D-ribose
• Synonyms: 1,3,5-TRI-O-BENZOYL-2-O-METHYL-ALPHA/BETA-D-RIBOSE;1,3,5-Tri-O-benzoyl-2-O-methyl-D-ribose;(2R,3R,4S)-2-hydroxy-4-methoxypentane-1,3,5-triyl tribenzoate;1,3,5-Tri-O-benzoyl-2-O-methyl-D-ribofuranose;1,3,5-Tri-O-benzoyl-2-O-methyl-a-D-ribose
• CAS NO: 68045-07-8
• Molecular Formula: C₂₇H₂₄O₈
• Molecular Weight: 477.48
• Mol File: 68045-07-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 598.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,3,5-Tri-O-benzoyl-2-O-methyl-D-ribose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Tri-O-benzoyl-2-O-methyl-D-ribose(68045-07-8)
• EPA Substance Registry System: 1,3,5-Tri-O-benzoyl-2-O-methyl-D-ribose(68045-07-8)

Safety Data

• Hazardous Substances Data: 68045-07-8(Hazardous Substances Data)

Usage

Uses

1,3,5-Tri-O-benzoyl-2-O-methyl-α-D-ribofuranose is used as a reactant in the preparation of 2''-O-methylpyrimidine ribonucleosides via stereoselective Vorbruggen glycosidation of pyrimidines. It is also used as a reactant in solid-phase synthesis, fluorescence, and ambiguous base pairing of canonical DNA nucleobases containing benzotriazole and 1,2,3-triazolo[4,5-d]pyrimidine.

Upstream product

• 186581-53-3 diazomethane 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 

Downstream Products

• 155006-24-9 1-(3,5-di-O-benzoyl-2-O-methyl-β-D-ribofuranosyl)-2-thio-4-(1H,3H)-pyrimidinone 
• 73793-16-5 N⁴-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine 
• 857684-40-3 1-(3,5-di-O-benzoyl-2-O-methyl-β-D-ribofuranosyl)-1H-1,2,3-benzotriazole 
• 52571-45-6 2'-O-methyl-N⁴-benzoylcytidine 
• 2140-72-9 2'-O-methylcytidine 
• 2140-76-3 2'-O-methyluridine 
• 172740-32-8 C₂₇H₂₆N₂O₈S 
• 113886-72-9 1-(2-O-methyl-β-D-ribofuranosyl)-2-thio-4-(1H,3H)-pyrimidinone 
• 2140-76-3 2'-O-methyluridine 
• 158966-50-8 N⁴-benzoyl-2'-O-methyl-5-methylcytidine 
• 55486-09-4 2'-O-Methyl-5-methyluridine 
• 857684-44-7 1-{5-O-[bis(4-methoxyphenyl)phenymethyl]-2-O-methyl-β-D-ribofuranosyl}-1H-1,2,3-benzotriazole 
• 158966-44-0 3',5'-bis-O-benzoyl-5-fluoro- 2'-O-methyluridine 
• 158966-43-9 3',5'-di-O-benzoyl-2'-O-methyl-5-methyluridine 

Relevant articles and documents

General preparative synthesis of 2'-O-methylpyrimidine ribonucleosides

A convergent and general approach to synthesizing 2'-O-methylpyrimidine ribonucleosides 4a-e-, 6, 7 on a multigram scale is described which begins with an improved procedure for making larger quantities of 2-O-methyl-1,3,5-tri-O-benzoyl-α-D-ribose. The sugar was reacted with the desired silylated pyrimidines at room temperature under Vorbruggen conditions. The crude products contained less than 10% of the α anomers and the desired β anomers were isolated by crystallization. The blocked nucleosides were then deprotected and isolated by standard methods.

Synthesis of tri-O-acyl-1,3,5-alpha-D-ribofuranoses specifically substituted in position 2

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