39686-83-4

Basic information

• Product Name: 1-O,2-O-(1-Methylethylidene)-α-D-glucofuranose=tris(methanesulfonate)
• Synonyms: 1-O,2-O-(1-Methylethylidene)-α-D-glucofuranose=tris(methanesulfonate)
• CAS NO: 39686-83-4
• Molecular Formula: C₁₂H₂₂O₁₂S₃
• Molecular Weight: 454.48
• Mol File: 39686-83-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 689.2°C at 760 mmHg
• Flash Point: 370.6°C
• Appearance: /
• Density: 1.57g/cm³
• Vapor Pressure: 4.64E-18mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 1-O,2-O-(1-Methylethylidene)-α-D-glucofuranose=tris(methanesulfonate)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O,2-O-(1-Methylethylidene)-α-D-glucofuranose=tris(methanesulfonate)(39686-83-4)
• EPA Substance Registry System: 1-O,2-O-(1-Methylethylidene)-α-D-glucofuranose=tris(methanesulfonate)(39686-83-4)

Safety Data

• Hazardous Substances Data: 39686-83-4(Hazardous Substances Data)

Usage

Chemical structure

A furanose ring with a 1-methylethylidene group attached to the 1 and 2 positions, and three methanesulfonate groups.

Purpose

Used as a protecting group for alcohols in organic synthesis.

Application

Commonly used in carbohydrate chemistry for protecting hydroxyl groups.

Selectivity

Allows for selective manipulations of other functional groups without affecting the protected hydroxyl group.

Reagent value

Valuable reagent for the synthesis of complex carbohydrate derivatives.

Industry applications

Used in the pharmaceutical and biotechnology industries.

InChI:InChI=1/C12H22O12S3/c1-12(2)21-10-9(24-27(5,17)18)8(20-11(10)22-12)7(23-26(4,15)16)6-19-25(3,13)14/h7-11H,6H2,1-5H3/t7-,8?,9+,10?,11?/m1/s1

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 74152-53-7 O¹,O²-isopropylidene-O³-methanesulfonyl-α-D-xylo-5,6-dideoxy-hex-5-enofuranose 
• 136787-16-1 6-S-benzoyl-1,2-O-isopropylidene-3,5-di-O-methanesulphonyl-6-thio-α-D-glucofuranose 
• 74152-53-7 1,2-O-isopropylidene-3-O-mesyl-α-xylo-5-hexenofuranose 

Relevant articles and documents

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1,2-MONO-, 1,2:3,5-DI-, AND 1,2:5,6-DI-O-ISOPROPYLIDENE-β-L-IDOFURANOSES; AN EXAMPLE OF 1,3-DIOXOLANE-1,3-DIOXANE ISOMERISATION

Simple preparative routes to 1,2-O-isopropylidene- and 1,2:5,6-di-O-isopropylideneβ-L-idofuranoses are described.The 1,2:5,6-diacetal is the kinetic product of the reaction of 1,2-O-isopropylidene-β-L-idofuranose with acetone and 2,2-dimethoxypropane in the presence of toluene-p-sulphonic acid but, during longer reaction times, isomerisation to 1,2:3,5-di-O-siopropylidene-β-L-idofuranose occurs, resulting in a approximately equal mixture of the two diacetals.