6743-85-7

Basic information

• Product Name: cinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• Synonyms: cinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS NO: 6743-85-7
• Molecular Weight: 464.469
• Mol File: 6743-85-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: cinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: cinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside(6743-85-7)
• EPA Substance Registry System: cinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside(6743-85-7)

Safety Data

• Hazardous Substances Data: 6743-85-7(Hazardous Substances Data)

Upstream product

• 50-99-7 D-glucose 
• 104-54-1 3-Phenylpropenol 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 
• 2595-07-5 allyl β-D-glucopyranoside 
• 98-80-6 phenylboronic acid 
• 10343-15-4 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 
• 108-24-7 acetic anhydride 
• 85026-55-7 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol 

Downstream Products

• 85026-55-7 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol 

Relevant articles and documents

Simple preparation of phenylpropenoid β-D-glucopyranoside congeners by Mizoroki-Heck type reaction using organoboron reagents

Palladium(II)-catalyzed carbon-carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside (3) and arylboronic acid congeners gave the corresponding cinnamyl 2,3,4,6-tetra-O-acetyl- β-d-glucopyranosides (4a-m) in good yield. Among them, coupling products 4a-m were converted to not only the naturally occurring phenylpropenoid β-d-glucopyranoside analogues (1a-e) but also the unnaturally ones (1f-m).

Chemoenzymatic syntheses of naturally occurring β-glucosides

Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4-nitrophenyl-β-D-glucopyranoside 4 using β- glucosidase from almonds gave stereoselectively β-D-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring β-glucosides in moderate yield. Among them, the β-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, respectively.