3868-04-0

Basic information

• Product Name: 1,5:3,4-Dianhydro-D-altropyranose
• Synonyms: 1,5:3,4-Dianhydro-D-altropyranose;1,6:3,4-Dianhydro-beta-D-altropyranose min. 98%;1,6:3,4-Dianhydro-2-D-altropyranose
• CAS NO: 3868-04-0
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.125
• Product Categories: Carbohydrates & Derivatives
• Mol File: 3868-04-0.mol

Chemical Properties

• Melting Point: 162-164°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Ethyl Acetate, Methanol
• CAS DataBase Reference: 1,5:3,4-Dianhydro-D-altropyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5:3,4-Dianhydro-D-altropyranose(3868-04-0)
• EPA Substance Registry System: 1,5:3,4-Dianhydro-D-altropyranose(3868-04-0)

Safety Data

• Hazardous Substances Data: 3868-04-0(Hazardous Substances Data)

Usage

Uses

1. Used in Organic Synthesis:
1,5:3,4-Dianhydro-D-altropyranose is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of molecules with potential applications in different industries.
2. Used in Pharmaceutical Industry:
1,5:3,4-Dianhydro-D-altropyranose can be used as a building block for the development of new pharmaceutical compounds. Its ability to form various derivatives makes it a valuable asset in the design and synthesis of novel drugs with potential therapeutic properties.
3. Used in Chemical Research:
As a compound with unique chemical properties, 1,5:3,4-Dianhydro-D-altropyranose can be utilized in chemical research to study the effects of structural modifications on the properties and reactivity of organic molecules. This can lead to a better understanding of the underlying principles governing chemical reactions and the development of new synthetic strategies.
4. Used in Material Science:
The unique structural features of 1,5:3,4-Dianhydro-D-altropyranose may also find applications in the field of material science. It could be used to develop new materials with specific properties, such as improved mechanical strength, thermal stability, or chemical resistance, depending on the desired application.

Upstream product

• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 23583-43-9 O³-(toluene-4-sulfonyl)-1,6-anhydro-β-D-altropyranose 
• 84207-46-5 3,4-di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 139437-39-1 1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose 
• 6167-32-4 1,6:3,4-dianhydro-2-O-tosyl-D-galactose 
• 3868-05-1 1,6-anhydro-2-O-(4-toluenesulfonyl)-β-D-glucopyranose 
• 949524-10-1 1,6-anhydro-3-deoxy-3-iodo-β-D-mannopyranose 
• 3868-03-9 1,6:2,3-dianhydro-β-D-mannopyranose 
• 50705-29-8 2-O-acetyl-1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 
• 71856-30-9 dianhydroaltrose 
• 37112-31-5 levoglucosenone 
• 50705-28-7 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 
• 1195607-39-6 O²-Benzoyl-1,6-anhydro-β-D-altropyranose 

Downstream Products

• 122291-80-9 3-amino-1,6-anhydro-β-D-mannopyranose 2-O,3-N-trichloroacetimidate 
• 213594-43-5 1,6:3,4-dianhydro-2-O-benzyl-β-D-altropyranose 
• 14168-65-1 mannosan 
• 90301-25-0 1,6:3,4-dianhydro-2-O-p-toluenesulfonyl-β-D-altropyranose 
• 872050-03-8 1,6-anhydro-4-deoxy-4-methyl-2-O-p-tolylsulfonyl-β-D-idopyranose 
• 872050-01-6 1,6-anhydro-4-deoxy-4-methyl-2-O-p-tolylsulfonyl-β-D-lyxopyranos-3-ulose 
• 58394-31-3 1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose 
• 194997-08-5 3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-keto-β-D-lyxo-hexopyranose 
• 552849-01-1 3-N-allylamino-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose 
• 552849-03-3 3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose 
• 552849-02-2 4-O-acetyl-3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose 
• 466646-22-0 (1R,2S,3S,4S,5R)-4-Benzyloxy-3-vinyl-6,8-dioxa-bicyclo[3.2.1]octan-2-ol 
• 251456-74-3 (1R,2S,3S,4S,5R)-2,4-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane-3-carbaldehyde 
• 251456-62-9 1,6-anhydro-2,4-di-O-benzyl-3-deoxy-3-C-vinyl-β-D-mannopyranose 

Relevant articles and documents

A Domino Epoxide Ring-Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars

A sterereospecific and efficient synthesis of thiosugars derived from levoglucosenone and methyl α-d-glucopyranoside was developed by a domino epoxide ring opening- xanthate migration to afford 1,3-oxathiolane-2-thiones in high yields. The stereochemical outcome of the new C–S bond was defined by the configuration of the starting materials. The 1,3-oxathiolane-2-thiones were subsequently submitted to a second tandem reaction affording the corresponding 2,3-episulfide alcohols. The thiosugars obtained are useful building blocks for the synthesis of thiooligosaccharides with potential biological properties.

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.

Skeletal rearrangements resulting from reactions of 1,6:2,3- and 1,6:3,4-dianhydro-β-d-hexopyranoses with diethylaminosulphur trifluoride

A complete series of eight 1,6:2,3- and 1,6:3,4-dianhydro-β-d- hexopyranoses were subjected to fluorination with DAST. The 1,6:3,4- dianhydropyranoses yielded solely products of skeletal rearrangement resulting from migration of the tetrahydropyran oxygen

Epoxide migration and pseudo-epoxide migration of 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses. Synthesis of some deoxy halo derivatives of 1,6-anhydro-β-D-hexopyranoses

Epoxide or pseudo-epoxide migration of 1,6:2,3-dianhydro- and 1,6:3,4-dianhydro-β-D-hexopyranoses was effected by treatment with aqueous sodium hydroxide or sodium iodide in acetone to give equilibrium mixtures. Various iodo derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared as potential intermediates for pseudo-epoxide migration. NMR was used for following the reaction mechanism of epoxide and pseudo-epoxide migrations and analysis of reaction mixtures. Experimental data were compared with DFT calculations. Chair-boat equilibration of 1,6-anhydro-3-deoxy-3-halo-β-D-glucopyranoses was discussed.

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 practical large-scale access to 1,6-anhydro-β-D-hexopyranoses by a solid-supported solvent-free microwave-assisted procedure

Microwave irradiation of 6-O-tosyl or 2,6-di-O-tosyl peracetylated hexopyranoses absorbed on basic alumina in a dry medium afforded the corresponding 1,6-anhydro-β-D-hexopyranoses. A direct access to 1,6:3,4-dianhydro-β-D-altropyranose (16) from D-glucose is also described.

An Expeditious and Stereocontrolled Preparation of 2-Azido-2-deoxy-β-D-glucopyranose Derivatives from D-Glucal

1,6-Anhydro-2-azido-2-deoxy-β-D-glucopyranose has been prepared by a two-step procedure from D-glucal and transformed into precursors useful in the synthesis of oligosaccharides.

PREPARATION OF 1,6:3,4-DIANHYDRO-β-D-ALTROPYRANOSE AS STARTING SUBSTANCE FOR THE SYNTHESIS OF 3-SUBSTITUTED D-MANNOSE DERIVATIVES

Acetolysis of 1,6:3,4-dianhydro-2-O-p-toluenesulfonyl-β-D-galactopyranose (I) gave 3,4-di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose (II) which was converted with sodium methoxide to 1,6:3,4-dianhydro-β-D-altropyranose (X).The 1,6-anhydride bond in diacetate II was cleaved with acetic anhydride or hydrogen bromide in acetic acid under formation of a mixture of anomeric tetraacetates of 2-O-p-toluenesulfonyl-D-glucopyranose or the corresponding acetates of α-D-glucopyranosyl bromide XIII and its 6-bromo-6-deoxy derivative XIV.