58394-31-3

Basic information

• Product Name: 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-ERYTHRO-HEX-2-ENOPRANOSE
• Synonyms: 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-ERYTHRO-HEX-2-ENOPRANOSE;.beta.-D-erythro-Hex-2-enopyranose, 1,6-anhydro-2,3-dideoxy-;1,6-Anhydro-2,3-dideoxy-b-D-erythro-hex-2-enopyranose
• CAS NO: 58394-31-3
• Molecular Formula: C₆H₈O₃
• Molecular Weight: 128.126
• Mol File: 58394-31-3.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-ERYTHRO-HEX-2-ENOPRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-ERYTHRO-HEX-2-ENOPRANOSE(58394-31-3)
• EPA Substance Registry System: 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-ERYTHRO-HEX-2-ENOPRANOSE(58394-31-3)

Safety Data

• Hazardous Substances Data: 58394-31-3(Hazardous Substances Data)

Usage

Chemical class

Carbohydrates

Specific type

Hexoses

Structure

Hexose ring with a double bond at the second carbon position

Modifications

Two hydroxyl groups missing at the third and fourth positions

Occurrence

Found in certain natural products

Applications

Used in the synthesis of various pharmaceuticals and bioactive compounds

Importance

Key intermediate in the biosynthesis of isoprenoid compounds

Relevance

Significant in the fields of organic chemistry and drug development

Upstream product

• 71021-15-3 1,6-anhydro-4-O-benzoyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranose 
• 13265-84-4 D-glucal 
• 157905-00-5 phenyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside 
• 454475-37-7 (1S,4R,5R)-4-(2-Nitro-phenylselanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-ene 
• 109-72-8 n-butyllithium 
• 90301-25-0 1,6:3,4-dianhydro-2-O-p-toluenesulfonyl-β-D-altropyranose 
• 3868-04-0 1,6:3,4-dianhydro-β-D-altropyranose 
• 50705-28-7 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 
• 37112-31-5 levoglucosenone 
• 2873-29-2 D-glucal triacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 50705-29-8 2-O-acetyl-1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 
• 71856-30-9 dianhydroaltrose 
• 58238-40-7 (1R,2R,4R,6R)-3,7,9-trioxatricyclo[4.2.1.0^2,4]nonan-5-one 

Downstream Products

• 33647-85-7 isolevoglucosenone 
• 40838-18-4 1,6-anhydro-4-O-benzyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranose 
• 58394-32-4 1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose 
• 331633-91-1 1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose 
• 331633-94-4 1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose 
• 331633-92-2 1,6-anhydro-4-O-p-methoxybenzyl-β-D-gulopyranose 
• 331633-93-3 1,6-anhydro-4-O-p-methoxybenzyl-β-D-gulopyranose 2,3-cyclic sulfate 
• 331633-97-7 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose 
• 26540-44-3 4-O-benzyl-1,6:2,3-dianhydro-β-D-allopyranoside 
• 33208-47-8 4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose 
• 110046-93-0 1,6-anhydro-4-O-benzyl-2-bromo-2-deoxy-β-D-glucopyranose 
• 148473-54-5 Acetic acid (1R,2R,3S,4R,5R)-2-benzyloxy-4-bromo-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester 
• 14086-08-9 (R)-2-(2-furyl)-1,2-ethanediol 

Relevant articles and documents

Diastereoselective Weitz-Scheffer epoxidation of levoglucosenone for the synthesis of isolevoglucosenone and derivatives

High-yielding epoxidation conditions for the cellulose pyrolysis product (?)-levoglucosenone (LGO) and 3-aryl derivatives of LGO have been developed. The reaction of LGO with hydrogen peroxide/base is known to give a Baeyer-Villiger reaction, however, it was found that the reactions of LGO or derivatives with tert-butylhydroperoxide/base affords solely epoxides through the Weitz-Scheffer reaction. A critical parameter in the successful isolation of the epoxide from LGO was to avoid all contact with water or alcohols during the reaction and workup. The epoxide products were reacted under Wharton conditions affording allylic alcohols and subsequent oxidation led to isolevoglucosenone or 3-arylisolevoglucosenone derivatives. Previously unreported reactions on isolevoglucosenone were then investigated.

New chiral building blocks and branched 1,6-anhydro sugars from regio- and stereoisomeric Cerny epoxides

The tandem epoxide→allyl alcohol rearrangement-cuprate cross-coupling previously described for the Cerny epoxide 1, to yield the allyl alcohol 2, was extended to the regioisomeric epoxy-tosylate 3, to yield allyl alcohol 4, and to the stereoisomeric epoxi

Chemoselective elaboration of O-linked glycopeptide mimetics by alkylation of 3-thioGalNAc

A critical branch point in mucin-type oligosaccharides is the β1 → 3 glycosidic linkage to the core α-N-acetylgalactosamine (GalNAc) residue. We report here a strategy for the synthesis of O-linked glycopeptide analogues that replaces this linkage with a