10300-20-6

Basic information

• Product Name: 5-O-Benzoyl-1,2-O-isopropylidene-3-O-Methyl-alpha-D-ribofuranose
• Synonyms: 5-O-Benzoyl-1,2-O-isopropylidene-3-O-Methyl-alpha-D-ribofuranose;3-O-Methyl-1,2-O-(1-methylethylidene)-alpha-D-ribofuranose benzoate
• CAS NO: 10300-20-6
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.3264
• Mol File: 10300-20-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 392.1°Cat760mmHg
• Flash Point: 171.5°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 2.34E-06mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: 5-O-Benzoyl-1,2-O-isopropylidene-3-O-Methyl-alpha-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-Benzoyl-1,2-O-isopropylidene-3-O-Methyl-alpha-D-ribofuranose(10300-20-6)
• EPA Substance Registry System: 5-O-Benzoyl-1,2-O-isopropylidene-3-O-Methyl-alpha-D-ribofuranose(10300-20-6)

Safety Data

• Hazardous Substances Data: 10300-20-6(Hazardous Substances Data)

Usage

General Description

5-O-Benzoyl-1,2-O-isopropylidene-3-O-Methyl-alpha-D-ribofuranose is a chemical compound that belongs to the class of ribofuranose derivatives. It is a carbohydrate derivative with a benzoyl group attached to the 5th carbon, an isopropylidene group attached to the 1st and 2nd carbons, and a methyl group attached to the 3rd carbon of the ribofuranose ring. 5-O-Benzoyl-1,2-O-isopropylidene-3-O-Methyl-alpha-D-ribofuranose has potential applications in organic synthesis and medicinal chemistry due to its unique structure and reactivity. It can also be used as a precursor for the synthesis of other complex molecules. The compound is of interest to researchers and chemists for its potential biological and pharmaceutical activities.

InChI:InChI=1/C16H20O6/c1-16(2)21-13-12(18-3)11(20-15(13)22-16)9-19-14(17)10-7-5-4-6-8-10/h4-8,11-13,15H,9H2,1-3H3

Upstream product

• 6612-91-5 ((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 
• 74-88-4 methyl iodide 
• 6698-46-0 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose 
• 6022-96-4 5-O-benzoyl-α-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 532-20-7 D-xylofuranose 
• 98-88-4 benzoyl chloride 
• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 

Downstream Products

• 58769-33-8 5-O-benzoyl-1,2-O-diacetyl-3-O-methyl-β-D-ribofuranose 
• 58800-57-0 5-O-benzoyl-1,2-O-diacetyl-3-O-methyl-α-D-ribofuranose 
• 10300-21-7 5-O-benzoyl-1,2-O-diacetyl-3-O-methyl-α/β-D-ribofuranose 

Relevant articles and documents

Total synthesis of mycalisine B

The first total synthesis of the marine nucleoside Mycalisine B-a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside-has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-O-acetyl-ribose and tetracyanoethylene. Key steps of the approach include: (1) I2 catalyzed acetonide formation from 1,2,3,5-tetra-O-acetylribose and acetone at large scale; (2) Vorbrüggen glycosylation using N4-benzoyl-5-cyano-6-bromo-7H-pyrrolo[2,3-d]pyrimidine as a nucleobase to avoid formation of N-3 isomer; (3) mild and scalable reaction conditions.

A total synthesis of mycalisine A

In this paper, we report a total synthesis of a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside, mycalisine A. Our synthetic strategy uses d-xylose as the starting material and Vorbrüggen glycosylation as the key step. Mycalisine A was synthesized in 11 steps with a 15% overall yield.