385421-76-1

Basic information

• Product Name: dibutyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranosyl phosphate
• Synonyms: dibutyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranosyl phosphate
• CAS NO: 385421-76-1
• Molecular Weight: 734.821
• Mol File: 385421-76-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: dibutyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranosyl phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: dibutyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranosyl phosphate(385421-76-1)
• EPA Substance Registry System: dibutyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranosyl phosphate(385421-76-1)

Safety Data

• Hazardous Substances Data: 385421-76-1(Hazardous Substances Data)

Upstream product

• 145852-76-2 3,6-di-O-benzyl-D-glucal 
• 123-76-2 levulinic acid 
• 3282-30-2 pivaloyl chloride 
• 107-66-4 dibutyl phosphate 
• 385421-75-0 3,6-di-O-benzyl-4-O-levulinoyl-glucal 

Downstream Products

• 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 
• 471930-59-3 n-pentenyl 3,6-dibenzyl-4-levulinoyl-2-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside 
• 471930-60-6 n-pentenyl 3,6-dibenzyl-2-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside 
• 385421-79-4 4-pentenyl 3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 385422-19-5 n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside 

Relevant articles and documents

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.