58394-31-3

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 
• 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 
• 37112-31-5 levoglucosenone 
• 58238-40-7 (1R,2R,4R,6R)-3,7,9-trioxatricyclo[4.2.1.0^2,4]nonan-5-one 
• 71856-30-9 dianhydroaltrose 
• 50705-29-8 2-O-acetyl-1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 2873-29-2 D-glucal triacetate 
• 50705-28-7 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 
• 3868-04-0 1,6:3,4-dianhydro-β-D-altropyranose 
• 157905-00-5 phenyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside 

Downstream Products

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

Relevant academic research and scientific papers

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.

The conversion of levoglucosenone into isolevoglucosenone

Levoglucosenone (1), a compound that will soon be available in tonne quantities through the pyrolysis of acid-treated lignocellulosic biomass, has been converted into isolevoglucosenone (2) using Wharton rearrangement chemistry. Treatment of compound 1 with alkaline hydrogen peroxide gave the γ-lactones 5 and 6 rather than the required epoxy-ketones 3 and/or 4. However, the latter pair of compounds could be obtained by an initial Luche reduction of compound 1, electrophilic epoxidation of the resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of compounds 3 and 4 with hydrazine then acetic acid followed by oxidation of the ensuing allylic alcohols finally afforded isolevoglucosenone (2). Details of the single-crystal X-ray analyses of epoxy-alcohols 9 and 10 are reported.

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

A new approach to isolevoglucosenone via the 2,3-sigmatropic rearrangement of an allylic selenide

A convenient method is described for the synthesis of isolevoglucosenone 5, via allylic selenide 3, and its rearrangement to allylic alcohol 4, followed by oxidation with manganese oxide. Isolevoglucosenone 5, is produced in 62% overall yield.

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

Thio-sugars. Part 5: From D-glucal to 3-deoxy-(1→2)-2-S-thiodisaccharides through isolevoglucosenone-a simple approach

A new synthesis of isolevoglucosenone and its stereoselective functionalization into 3-deoxy-(1-2)-2-S-thiodisaccharides is described. The base-catalyzed conjugate addition of 1-thiosugars to isolevoglucosenone followed by the reduction of the C-4 keto function constitute a new two-step general approach to these classes of biologically important thio-sugars. Copyright (C) 2000 Elsevier Science Ltd.

A ready method for generating oxycarbinyl radicals for conjugate-addition-alkylation or radical cyclization reactions

A ready method is described from generating oxycarbinyl radicals from alcohols, acetals and aldehydes which involves periodic addition of di-tert-butyl-hyponitrite (DBH) to a refluxing solution of the precursor.The resulting radicals may be trapped intermolecularly by α-enones in conjugate-addition-alkylation reactions, or intermolecularly in ring-forming reactions.Typically, small portions of DBH are added every 10-15 minutes until the reactant of interest has been consumed. Keywords: conjugate addition / carbohydrate α-enones / oxycarbinyl radicals