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

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 

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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.