253683-26-0

Basic information

• Product Name: dibutyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside phosphate
• Synonyms: dibutyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside phosphate
• CAS NO: 253683-26-0
• Molecular Weight: 750.982
• Mol File: 253683-26-0.mol

Chemical Properties

• CAS DataBase Reference: dibutyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: dibutyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside phosphate(253683-26-0)
• EPA Substance Registry System: dibutyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside phosphate(253683-26-0)

Safety Data

• Hazardous Substances Data: 253683-26-0(Hazardous Substances Data)

Upstream product

• 3282-30-2 pivaloyl chloride 
• 145852-76-2 3,6-di-O-benzyl-D-glucal 
• 253683-41-9 1,5-anhydro-4-O-tert-butyldimethylsilyl-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol 
• 107-66-4 dibutyl phosphate 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 511511-30-1 ((1S,3R,4R,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]hept-4-yloxy)-tert-butyl-dimethyl-silane 

Downstream Products

• 385422-18-4 n-pentenyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 373606-36-1 3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 385421-81-8 n-pentenyl 4,6-di-O-benzyl-3-O-levulinyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 385421-82-9 n-pentenyl 4,6-di-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 385421-79-4 4-pentenyl 3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 373606-35-0 dibutyl 3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside phosphate 

Relevant articles and documents

Oligosaccharide synthesis with glycosyl phosphate and dithiophosphate triesters as glycosylating agents

Described is an efficient one-pot synthesis of α- and β-glycosyl phosphate and dithiophosphate triesters from glycals via 1,2-anhydrosugars. Glycosyl phosphates function as versatile glycosylating agents for the synthesis of β-glucosidic, β-galactosidic,

Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks

A linear synthesis of a fully protected H-type II blood group determinant pentasaccharide utilizing glycosyl phosphate and glycosyl trichloroacetimidate building blocks is reported. Envisioning an automated solid-phase synthesis of blood group determinants, the utility of glycosyl phosphates in the stepwise construction of complex oligosaccharides, such as the H-type II antigen, is demonstrated. Installation of the central glucosamine building block required the screening of a variety of nitrogen protecting groups to ensure good glucosamine donor reactivity and protecting group compatibility. The challenge to differentiate C2 of the terminal galactose in the presence of other hydroxyl and amine protecting groups prompted us to introduce the 2-(azidomethyl)benzoyl group as a novel mode of protection for carbohydrate synthesis. The compatibility of this group with traditionally employed protecting groups was examined, as well as its use as a C2 stereodirecting group in glycosylations. The application of the 2-(azidomethyl)benzoyl group along with a systematic evaluation of glycosyl donors allowed for the completion of the pentasaccharide and provides a synthetic strategy that is expected to be generally amenable to the solid support synthesis of blood group determinants.

Solid-phase oligosaccharide synthesis: preparation of complex structures using a novel linker and different glycosylating agents.

[formula: see text] A beta-(1-->4)-linked trisaccharide was prepared in 53% yield on a polymer support using glycosyl phosphates and released by cross-metathesis of a novel linker to reveal the anomeric n-pentenyl glycoside. Heptasaccharide 33 was prepared in 9% yield in 14 steps.