385422-19-5

Basic information

• Product Name: n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside
• Synonyms: n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside
• CAS NO: 385422-19-5
• Molecular Weight: 610.745
• Mol File: 385422-19-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside(385422-19-5)
• EPA Substance Registry System: n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside(385422-19-5)

Safety Data

• Hazardous Substances Data: 385422-19-5(Hazardous Substances Data)

Upstream product

• 821-09-0 n-Pent-4-enyl alcohol 
• 385421-76-1 dibutyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranosyl phosphate 
• 3282-30-2 pivaloyl chloride 
• 123-76-2 levulinic acid 
• 145852-76-2 3,6-di-O-benzyl-D-glucal 
• 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 

Relevant articles and documents

Linear synthesis of the tumor-associated carbohydrate antigens Globo-H, Ssea-3, and Gb3

The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult α-(1→-4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the β-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the β-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.