58109-18-5

Basic information

• Product Name: 1,2:5,6-DI-O-CYCLOHEXYLIDENE-3-O-METHYLSULFONYL-ALPHA-D-ALLOFURANOSE
• Synonyms: 1,2:5,6-DI-O-CYCLOHEXYLIDENE-3-O-METHYLSULFONYL-ALPHA-D-ALLOFURANOSE
• CAS NO: 58109-18-5
• Molecular Formula: C19H30O8S
• Molecular Weight: 418.5017
• Mol File: 58109-18-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2:5,6-DI-O-CYCLOHEXYLIDENE-3-O-METHYLSULFONYL-ALPHA-D-ALLOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:5,6-DI-O-CYCLOHEXYLIDENE-3-O-METHYLSULFONYL-ALPHA-D-ALLOFURANOSE(58109-18-5)
• EPA Substance Registry System: 1,2:5,6-DI-O-CYCLOHEXYLIDENE-3-O-METHYLSULFONYL-ALPHA-D-ALLOFURANOSE(58109-18-5)

Safety Data

• Hazardous Substances Data: 58109-18-5(Hazardous Substances Data)

Usage

Chemical compound

A substance formed from the sugar molecule D-allofuranose.

Derived from

D-allofuranose, a monosaccharide.

Common use

As a protecting group for hydroxyl groups in organic synthesis reactions.

Contains

Two cyclohexylidene rings.

Contains

A methylsulfonyl group.

Function of cyclohexylidene rings

Temporarily block the reactivity of certain hydroxyl groups.

Allows

Selective chemical reactions to occur in other parts of the molecule.

Function of methylsulfonyl group

Acts as a protective group and stabilizes the molecule during reactions.

Value

Controls the reactivity and selectivity of chemical reactions involving sugar molecules in organic chemistry.

Upstream product

• 18546-21-9 1,2:5,6-di-O-cyclohexylidene-α-D-ribo-3-hexofuranose-3-ulose 
• 18608-94-1 1,2:5,6-di-O-cyclohexylidene-α-D-allofuranose 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 64503-66-8 methyl 2-O-benzoyl-5,6-O-cyclohexylidene-3-deoxy-α-D-ribo-hexofuranoside 
• 64503-64-6 methyl 2-O-benzoyl-5,6-O-cyclohexylidene-3-deoxy-β-D-arabino-hexofuranoside 

Relevant articles and documents

The Use of Grignard Reagents in the Synthesis of Carbohydrates. I. The Synthesis of Deoxy and Branched-chain Deoxy Sugars

Two branched-chain deoxy sugars, methyl 5,6-O-cyclohexylidene-3-deoxy-2-C-methyl-β-D-arabino-hexofuranoside and its α-D-ribo isomer, were easily prepared by the one-step reaction of methyl 5,6-O-cyclohexylidene-3-O-mesyl-β-D-allofuranoside (3a) with methylmagnesium iodide.Similarly, the corresponding α-mesylate (4a) gave methyl 5,6-O-cyclohexylidene-3-deoxy-2-C-methyl-α-D-ribo-hexofuranoside.It was demonstrated that these reactions involved 1,2-hydride shifts.The reactions of 3a and 4a with t-butylmagnesium bromide yielded two deoxy sugars, methyl 5,6-O-cylohexylidene-3-deoxy-β-D-arabino-hexofuranoside and the corresponding α-D-ribo isomer, respectively.Under certain reaction conditions with the Grignard reagents, the sulfonate (3a) afforded dimeric compounds, in which two furanose rings were directly bound with a carbon-carbon bond.A convenient method for the preparation of the sulfonates (3a and 4a) is also reported.