1384472-16-5

Basic information

• Product Name: 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside
• Synonyms: 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside
• CAS NO: 1384472-16-5
• Molecular Weight: 452.577
• Mol File: 1384472-16-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside(1384472-16-5)
• EPA Substance Registry System: 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside(1384472-16-5)

Safety Data

• Hazardous Substances Data: 1384472-16-5(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 81336-89-2 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 1384472-23-4 C₂₂H₃₄O₈Si 

Relevant articles and documents

The Origin of High Stereoselectivity in Di-tert-butylsilylene-Directed α-Galactosylation

The origin of the high α(1,2-cis)-stereoselectivity in the reaction of galactosyl and galactosaminyl donors with a di-tert-butylsilylene (DTBS) group with several nucleophiles has been elucidated by means of experimental and computational approaches. DTBS overcomes any other cyclic protecting groups examined to date and the β(1,2-trans)-directing effect due to the neighboring participation by CO groups at C2. Requirements for the α(1,2-cis)-stereoselectivity are as follows: (1) generation of an oxocarbenium ion; (2) a galacto-type glycosyl donor with a cyclic protecting group bridging O4 and O6 to form a six-membered ring; (3) through-space electron donation from O4 and O6 into the empty p-orbital of the anomeric carbon to stabilize the oxocarbenium intermediate; (4) steric hindrance due to bulky alkyl substituents on the cyclic protecting group to prevent nucleophilic attack from the β-face; and (5) a 4,6-O-silylene structure. Furthermore, it was found that the strong stereodirecting effect of the DTBS group was unique and specific among the various cyclic protecting groups examined.