104758-89-6

Basic information

• Product Name: methyl 4,6-O-benzylidene-2-O-pivaloyl-α-D-glucopyranoside
• Synonyms: methyl 4,6-O-benzylidene-2-O-pivaloyl-α-D-glucopyranoside
• CAS NO: 104758-89-6
• Molecular Weight: 366.411
• Mol File: 104758-89-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: methyl 4,6-O-benzylidene-2-O-pivaloyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-2-O-pivaloyl-α-D-glucopyranoside(104758-89-6)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-2-O-pivaloyl-α-D-glucopyranoside(104758-89-6)

Safety Data

• Hazardous Substances Data: 104758-89-6(Hazardous Substances Data)

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 3282-30-2 pivaloyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 3377-92-2 vinyl pivalate 

Downstream Products

• 50-99-7 D-glucose 
• 112669-91-7 Methyl 4,6-O-benzylidene-2-O-(t-butyldiphenylsilyl)-α-D-ribo-hexopyranosid-3-uloside 
• 130130-72-2 methyl (R)-4,6-O-benzylidene-2-O-(2,2-dimethylpropanoyl)-α-D-ribohexopyranosid-3-ulose 
• 112669-93-9 Methyl 4,6-O-benzylidene-3-deoxy-3-C-<(E)-methoxycarbonylmethylene>-2-O-(t-butyldiphenylsilyl)-α-D-ribo-hexopyranoside 
• 130130-73-3 Methyl 4,6-O-benzylidene-3-C-(methoxycarbonylmethylene)-3-deoxy-2-O-pivaloyl-α-D-ribo-hexopyranoside 
• 112669-95-1 Methyl 4,6-O-benzylidene-3-deoxy-3-C-(methoxycarbonylmethylene)-α-D-ribo-hexopyranoside 
• 112669-96-2 Methyl 4,6-O-benzylidene-3-deoxy-3-C-(methoxycarbonylmethylene)-α-D-allopyranoside 
• 112669-98-4 Methyl 4,6-O-benzylidene-3-deoxy-3-(prop-2-yloxycarbonyl)-2,3-butyrolactone-α-D-allopyranoside 
• 112669-97-3 Methyl 4,6-O-benzylidene-3-deoxy-3-(ethoxycarbonyl)-2,3-butyrolacto-α-D-allopyranoside 

Relevant articles and documents

SELECTIVE LIPASE-CATALYZED ACYLATION OF 4,6-O-BENZYLIDENE-D-GLUCOPYRANOSIDES TO SYNTHETICALLY USEFUL ESTERS

Simple and regioselective lipase-catalyzed acylation of compounds 1 and 4 with synthetically useful esters such as benzoates, chloroacetates, pivaloates and levulinates is described.

Wittig Reaction: Domino Olefination and Stereoselectivity DFT Study. Synthesis of the Miharamycins' Bicyclic Sugar Moiety

2-O-Acyl protected-d-ribo-3-uloses reacted with [(ethoxycarbonyl)methylene]triphenylphosphorane in acetonitrile to afford regio- and stereoselectively 2-(Z)-alkenes in 10-60 min under microwave irradiation. This domino reaction is proposed to proceed via tautomerization of 3-ulose to enol, acyl migration, tautomerization to the 3-O-acyl-2-ulose, and Wittig reaction. Alternatively, in chloroform, regioselective 3-olefination of 2-O-pivaloyl-3-uloses gave (E)-alkenes, key precursors for the miharamycins' bicyclic sugar moiety.

Regioselective Acylation of Hexopyranosides with Pivaloyl Chloride

-