201603-61-4

Basic information

• Product Name: (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol
• Synonyms: (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol
• CAS NO: 201603-61-4
• Molecular Weight: 356.419
• Mol File: 201603-61-4.mol

Chemical Properties

• CAS DataBase Reference: (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol(201603-61-4)
• EPA Substance Registry System: (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol(201603-61-4)

Safety Data

• Hazardous Substances Data: 201603-61-4(Hazardous Substances Data)

Upstream product

• 118968-02-8 (1S)-(1,3/2,4)-1,2-dibenzyloxy-3-hydroxy-4-hydroxymethylcyclohex-5-ene 
• 215303-21-2 (2S,3S,4S,5S,6R)-4,5,6-Tris-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-heptanoic acid methyl ester 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 869476-28-8 ethyl (2S,3R,4S,5S)-4,5-bis(benzyloxy)-3-hydroxy-2-vinylhept-6-enoate 
• 869476-29-9 ethyl (1S,4S,5S,6R)-4,5-bis(benzyloxy)-6-hydroxycyclohex-2-enecarboxylate 
• 869476-25-5 methyl 2,3-di-O-benzyl-5-deoxy-5-iodo-D-xylofuranoside 
• 869476-26-6 2,3-di-O-benzyl-2,3-dihydroxypent-4-enal 
• 201603-59-0 (1R,2R,3S,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-iodomethyl-7-oxa-bicyclo[4.1.0]heptane 
• 215303-20-1 (E)-(4S,5R,6R)-4,5,6-Tris-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-hept-2-enoic acid methyl ester 
• 201603-46-5 methyl (2E,4R,5R,6S)-4,5,6-tri(benzyloxy)-2,7-octadienoate 
• 201603-58-9 Formic acid (1R,2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-2-iodo-6-iodomethyl-cyclohexyl ester 
• 201603-43-2 tert-Butyl-dimethyl-((2R,3R,4S)-2,3,4-tris-benzyloxy-hex-5-enyloxy)-silane 
• 201603-57-8 (3aR,4R,5S,6R,7S,7aR)-4,5,6-Tris-benzyloxy-7-iodo-octahydro-benzofuran-2-ol 
• 185987-56-8 2-(R)-3-(S)-4-(R)-tribenzyloxy-5-t-butyldimethylsilyloxy-pentanal 

Downstream Products

• 126661-83-4 cyclophellitol 

Relevant articles and documents

Exploring functional cyclophellitol analogues as human retaining beta-glucosidase inhibitors

The natural product, cyclophellitol and its aziridine analogue are potent mechanism-based retaining β-glucosidase inhibitors. In this paper we explore the inhibitory potency of a number of cyclophellitol analogues against the three human retaining β-glucosidases, GBA, GBA2 and GBA3. We demonstrate that N-alkyl cyclophellitol aziridine is at least equally potent in inhibiting the enzymes evaluated as its N-acyl congener, whereas the N-sulfonyl analogue is a considerably weaker inhibitor. Our results complement the literature on the inhibitory potency of cyclophellitol analogues and hold promise for the future design of more effective activity-based retaining glycosidase probes with respect to probe stability in physiological media.

Synthesis of cyclophellitol, cyclophellitol aziridine, and their tagged derivatives

Cyclitol epoxides and aziridines are potent and selective irreversible inhibitors of retaining glycosidases. We have previously reported on our studies on the use of activity-based probes derived from cyclophellitol and from its aziridine analogue for activity-based profiling of retaining β-glucosidases in vitro, in situ, and in some examples also in vivo. In this work we disclose full details of the synthesis, purification, and analysis of a comprehensive panel of cyclophellitol analogues, all featuring the β-glucose configuration and designed as tools for selective inhibition and/or imaging of human acid glucosylceramidase (epoxides) or as broad-spectrum probes for retaining β-glucosidases (aziridines).

A short synthesis of (+)-cyclophellitol

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Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

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