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
• Article Data: 3

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

General Description

1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose, also known as benzoylated ribofuranose, is a chemical compound that is a derivative of ribofuranose, a form of ribose. It is a white to off-white solid that is used in organic chemical synthesis. 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSE is commonly used in the process of synthesizing nucleosides, nucleotides, and other important biomolecules. Its acetyl and benzoyl groups make it a versatile building block in the creation of various pharmaceutical and biotechnological products. Additionally, the compound is an important intermediate in the synthesis of anti-viral and anti-cancer drugs. Its structure and properties make it a highly useful chemical in the field of organic chemistry.

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

• 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 
• 16755-07-0 showdomycin 
• 121682-60-8 2,3,5-tri-O-benzyl-β-D-ribofuranosyl azide 
• 91110-25-7 2,3,5,2',3',5'-hexa-O-Benzyl-(α-D-ribofuranosyl α-D-ribofuranoside) 
• 98815-79-3 (2R,3R,3aS,9bR)-3-benzyloxy-2-benzyloxymethyl-3,3a,5,9b-tetrahydro-2H-furo<3,2-c><2>benzopyran 

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 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,