58871-06-0

Basic information

• Product Name: 3,6-DI-O-BENZOYL-D-GLUCAL
• Synonyms: 3,6-DI-O-BENZOYL-D-GLUCAL
• CAS NO: 58871-06-0
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 388.37
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 58871-06-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 129-134 °C(lit.)
• Appearance: /
• CAS DataBase Reference: 3,6-DI-O-BENZOYL-D-GLUCAL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-DI-O-BENZOYL-D-GLUCAL(58871-06-0)
• EPA Substance Registry System: 3,6-DI-O-BENZOYL-D-GLUCAL(58871-06-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 58871-06-0(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 13265-84-4 D-glucal 
• 136573-59-6 1,5-anhydro-3,4-di-O-benzoyl-6-O-t-butyldimethylsilyl-2-deoxy-D-arabino-hex-1-enitol 

Downstream Products

• 121328-62-9 C₄₇H₄₅IO₁₀ 
• 128358-52-1 O-<2-(benzenesulfonamido)-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl>-β-(1<*>4)-1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabinohex-1-enopyranose 
• 121328-71-0 C₆₅H₈₂I₂O₁₄Si₂ 
• 121328-72-1 C₆₅H₈₂I₂O₁₄Si₂ 
• 81562-22-3 1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-4-O-mesyl-D-arabino-hex-1-enitol 
• 121328-68-5 (2R,3S,4R)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-iodo-tetrahydro-pyran-2-yloxy)-2-hydroxymethyl-3,4-dihydro-2H-pyran-4-ol 
• 121351-29-9 (2R,3R,4R)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-iodo-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran 
• 121328-64-1 C₅₉H₆₆O₁₆ 
• 121351-28-8 C₅₉H₆₄I₂O₁₆ 
• 121328-63-0 C₅₉H₆₄I₂O₁₆ 
• 36396-43-7 Methyl-3,4,6-tri-O-benzoyl-2-desoxy-β-D-lyxo-hexopyranosid 
• 36396-42-6 Methyl-3,4,6-tri-O-benzoyl-2-desoxy-α-D-lyxo-hexopyranosid 
• 34948-79-3 1,5-anhydro-3,4,6-tri-O-benzoyl-2-deoxy-D-lyxo-hex-1-enitol 
• 81562-23-4 1,4,6-tri-O-benzoyl-2,3-dideoxy-α-D-threo-hex-2-enopyranose 

Relevant articles and documents

TRITERPENE SAPONIN SYNTHESIS, INTERMEDIATES AND ADJUVANT COMBINATIONS

The present application relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, and intermediates thereto. The application also provides pharmaceutical compositions comprising compounds of the present invention and methods of using said compounds or compositions in the treatment of and immunization for infectious diseases.

Stereocontrolled intramolecular aziridination of glycate: Ready access to aminoglycosides and mechanistic insights from DFT studies

Stereocontrolled intramolecular aziridination of the glycal-derived sulfamates offers a highly efficient strategy to divergently prepare aminoglycosides. Rhodium-catalyzed nitrogen-atom transfer to C=C bonds formed semistable aziridines, which were subjected to various nucleophiles (C, O, S, and N) to give cyclic sulfamate-containing aminosugar derivatives selectively. The second nucleophilic displacement of sulfonyloxy moieties of [1,2,3]-oxathiazepane-2,2-dioxides allows straightforward access to aminoglycosides with selective α- or β-linkages. This approach is operationally simple, complements existing methods, and is a versatile protocol for the synthesis of polyfunctionalized amino sugars. In addition, the mechanism of the rhodium-catalyzed intramolecular aziridination of glycals and its ring-opening reaction was extensively studied by using DFT calculations.

CATION-EXCHANGE RESIN-CATALYZED ADDITION OF METHANOL TO BENZOYLATED 1,5-ANHYDRO-2-DEOXY-D-HEX-1-ENITOLS

1,5-Anhydro-3,4,5-tri-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (1) was boiled under reflux with methanol and AG 50W-X8 cation-exchange resin.A two-product mixture of glycosides (2 and 3) was obtained in 38percent yield, together with 19percent of unreacted material. 1,5-Anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (7) was prepared from 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol by selective benzoylation, from wich the corresponding 4-methansulphonate 8 was obtained.Treatment of 8 with sodium benzoate in hexamethylphosphoric triamide for 72 h at 100 deg C afforded 1,5-anhydro-3,4,6-tri-O-benzoyl-2-deoxy-D-xylo-hex-1-enitol (9) in 52percent yield.An unknow byproduct (B), tentitatively shown to be a tri-O-benzoyl-D-hex-2-enopyranose analog, was also isolated in 14percent yield.The 270-MHz n.m.r. spectrum of B was analyzed in terms of its J1,3, J2,4 and J4,5 coupling constant in relation to the various configurational and conformational possibilities for hex-2-enopyranose, and was identified as 1,4,6-tri-O-benzoyl-2,3-dideoxy-α-D-threo-hex-2-enopyranose having the oH5 conformation.The analysis presented should also be applicable to pent-2-enopyranose systems.When 9 was treated with methanol in the presence of AG 50W-X8 cation-exchange resin, a mixture of glycosides 4 and 5 was obtained in 47percent yield.The low yields were attributed to methanolysis of the benzoyl groups during the reaction.