91110-24-6

Basic information

• Product Name: 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSE
• Synonyms: B-D-RIBOFURANOSE-1-ACETATE-2,3,5-TRIBENZOATE;1-ACETYL-2,3,5-TRIBENZOY-B-D-RIBOFURANOSE;1-ACETYL-2,3,5-TRIBENZOYL-B-D-RIBOFURANOSE;1-ACETYL-2,3,5-TRIBENZOYL-BETA-D-RIBOFURANOSE;1-ACETYL-2,3,5-TRIBENZOYL-BETA-D-RIBOFURANOSIDE;2,3,5-TRI-O-BENZOYL-1-O-ACETYL-BETA-D-RIBOFURANOSE;1-O-ACETYL-2,3,5-TRIBENZOYL-BETA-D-RIBOFURANOSIDE;1-O-ACETYL-2,3,5-TRI-O-BENZOYL-B-D-RIBOFURANOSE
• CAS NO: 91110-24-6
• Molecular Formula: C₂₈H₃₀O₆
• Molecular Weight: 504.48
• EINECS: 230-220-4
• Mol File: 91110-24-6.mol

Chemical Properties

• Melting Point: 128-130 °C
• Boiling Point: 575.655oC at 760 mmHg
• Flash Point: 245.026oC
• Appearance: /
• Density: 1.20
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.589
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSE(91110-24-6)
• EPA Substance Registry System: 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSE(91110-24-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 91110-24-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemical Synthesis:
1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSE is used as a versatile building block for the synthesis of various pharmaceutical and biotechnological products due to its acetyl and benzoyl groups.
Used in Pharmaceutical Industry:
1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSE is used as an important intermediate in the synthesis of anti-viral and anti-cancer drugs, contributing to the development of new therapeutic agents.
Used in Biomolecular Synthesis:
1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSE is used as a key component in the process of synthesizing nucleosides, nucleotides, and other important biomolecules, playing a crucial role in the creation of biologically active compounds.

InChI:InChI=1/C28H30O6/c1-21(29)33-28-27(32-19-24-15-9-4-10-16-24)26(31-18-23-13-7-3-8-14-23)25(34-28)20-30-17-22-11-5-2-6-12-22/h2-16,25-28H,17-20H2,1H3/t25-,26-,27-,28-/m1/s1

Upstream product

• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 108-24-7 acetic anhydride 
• 89361-52-4 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranose 

Downstream Products

• 130817-02-6 isopropyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 
• 92414-07-8 isopropyl 2,3,5-tri-O-benzyl-α-D-ribofuranoside 
• 121682-57-3 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(1-phenyl-vinyloxy)-tetrahydro-furan 
• 93836-20-5 2-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)acetophenone 
• 92414-05-6 octadecyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 
• 148744-16-5 Diphenyl(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)phosphine Oxide 
• 52492-43-0 2,5-anhydro-3,4,6-tri-O-benzyl-D-allononitrile 
• 82267-01-4 (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile 
• 82267-02-5 2,3,5-tri-O-benzyl-α-D-ribofuranosyl cyanide 
• 149118-07-0 (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-phenylsulfanyl-tetrahydro-furan 
• 86883-48-9 methyl 6-O-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 86883-47-8 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-α-D-glucopyranoside 
• 57378-89-9 2,3,5-tri-O-benzyl-D-ribofuranosyl bromide 
• 107961-04-6 α-1-deoxy-1-C-(phenylthio)-2,3,5-tri-O-benzyl-D-ribofuranose 

Relevant articles and documents

Chemical investigations in the synthesis of O-serinyl aminoribosides

Glycosylation involving d-ribose derivatives and various N-protected tert-butyl l-serinates can be achieved efficiently by careful choice of the activation method at the anomeric position and of the Lewis acid promoter. The conditions described allow the major formation of the β-anomer required for further elaboration to liposidomycin and caprazamycin analogues.

A CONVENIENT SYNTHESIS OF C-α-D-RIBOFURANOSYL COMPOUNDS FROM 1-O-ACETYL-2,3,5-TRI-O-BENZYL-β-D-RIBOSE BY THE PROMOTION OF TRIPHENYLMETHYL PERCHLORATE

In the presence of a catalytic amount of triphenylmethyl perchlorate (trityl perchlorate), 1-O-acetyl-2,3,5-tri-O-benzyl-β-D-ribose stereoselectively reacted with trimethylsilyl nucleophiles, such as trimethylsilyl enol ether, allylsilane, and trimethylsi

A FACILE SYNTHESIS OF α-GLUCOSIDES AND α-RIBOSIDES FROM THE CORRESPONDING 1-O-ACYL SUGARS AND ALCOHOLS IN THE PRESENCE OF TRITYL PERCHLORATE

In the presence of trityl perchlorate, 1-O-bromoacety-β-D-glucose stereoselectively reacts with alcohols to give the corresponding α-glucosides in good yields.The similar reaction of 1-O-acetyl-β-D-ribose affords the corresponding β-ribosides exclusively,