228399-00-6

Basic information

• Product Name: 2,5-anhydro-3,6-di-O-benzoyl-D-allose ethylene acetal
• Synonyms: 2,5-anhydro-3,6-di-O-benzoyl-D-allose ethylene acetal
• CAS NO: 228399-00-6
• Molecular Weight: 414.412
• Mol File: 228399-00-6.mol

Chemical Properties

• CAS DataBase Reference: 2,5-anhydro-3,6-di-O-benzoyl-D-allose ethylene acetal(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-anhydro-3,6-di-O-benzoyl-D-allose ethylene acetal(228399-00-6)
• EPA Substance Registry System: 2,5-anhydro-3,6-di-O-benzoyl-D-allose ethylene acetal(228399-00-6)

Safety Data

• Hazardous Substances Data: 228399-00-6(Hazardous Substances Data)

Upstream product

• 157506-36-0 2,5-anhydro-4-O-benzoyl-3,6-di-O-methanesulfonyl-D-glucose ethylene acetal 
• 157506-35-9 2,5-anhydro-3,6-di-O-methanesulfonyl-D-glucose ethylene acetal 
• 98-88-4 benzoyl chloride 
• 157506-37-1 2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-glucose ethylene acetal 

Downstream Products

• 228399-06-2 C₂₃H₂₁F₃O₁₀S 
• 294664-46-3 3(5)-carbomethoxy-4-(2,5-di-O-benzoyl-3-O-methanesulfonyl-β-D-ribofuranosyl)pyrazole 
• 294664-45-2 C₂₄H₂₄O₁₀S 
• 615249-45-1 C₂₀H₁₈FNO₅S 
• 228399-14-2 C₂₂H₂₁FO₇ 
• 615249-50-8 C₂₂H₂₁NO₇ 
• 615249-43-9 C₂₀H₁₈FNO₆ 
• 615249-44-0 C₂₀H₁₆FNO₅ 
• 615249-42-8 C₂₀H₁₇FO₆ 
• 228399-13-1 2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulose ethylene acetal 
• 60084-12-0 2-(4-carboethoxythiazol-2-yl)-5-((benzoyloxy)methyl)furan 
• 228399-02-8 2,5-anhydro-3,6-di-O-benzoyl-4-O-methanesulfonyl-D-allose ethylene acetal 
• 360577-78-2 5-(3-azido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)tetrazole 
• 410082-11-0 2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulononitrile 

Relevant articles and documents

Synthesis and biological evaluation of two novel 2′-substituted tiazofurin analogues

Two novel tiazofurin analogues, 2-(2-benzamido-2-deoxy-β-d- ribofuranosyl)thiazole-4-carboxamide 4 and 2-(2-azido-2-deoxy-β-d- ribofuranosyl)thiazole-4-carboxamide 5, have been synthesized starting from d-glucose and evaluated for their in vitro cytotoxicity against several human leukaemia and solid tumour cell lines.

Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties

3(5)-Carboxamido-4-(β-D-ribofuranosyl)pyrazoles bearing 2′-benzamido (15) and 3′-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-β-D-ribofuranose (19) and 3-azido-3-deoxy-β-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus.

Stereospecific synthesis of two novel cytotoxic pyrazole C-nucleosides from D-glucose

A multistep stereospecific synthesis of two novel pyrazole C-nucleosides 12 and 21 has been achieved starting from D-glucose, by utilizing the 2,5- anhydro-D-glucose ethylene acetal derivative 1 as a divergent intermediate. The C-nucleoside 12 was shown to be a moderate inhibitor of the in vitro growth of N2a and BHK 21 tumor cell lines, whereas 21 showed a moderate cytotoxic activity only against N2a cells. (C) 2000 Published by Elsevier Science Ltd.

Preparation of 2,5-anhydro-3,4,6-tri-O-benzoyl-D-allononitrile from D- glucose

2,5-Anhydro-3,4,6-tri-O-benzyoyl-D-allononitrile has been extensively used in the synthesis of C-nucleosides with potential antitumor and/or antivirial properties. Three independent synthesis of 1 have already been described starting from D-ribose The authors now report a new synthesis of 1 from D-glucose.