178181-75-4

Basic information

• Product Name: (S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester
• Synonyms: (S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester
• CAS NO: 178181-75-4
• Molecular Weight: 886.127
• Mol File: 178181-75-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester(178181-75-4)
• EPA Substance Registry System: (S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester(178181-75-4)

Safety Data

• Hazardous Substances Data: 178181-75-4(Hazardous Substances Data)

Upstream product

• 122350-52-1 (4S)-5-benzyloxy-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid 
• 137792-66-6 phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-D-galactal 
• 178181-74-3 benzyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-hydroxypentanoate 
• 214468-40-3 1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside 

Relevant articles and documents

Use of acid-labile protective groups for carbohydrate moieties in synthesis of glycopeptides related to type II collagen

β-D-Galactopyranosyl and α-D-glucopyranosyl-β-D-galactopyranosyl moieties carrying silyl, isopropylidene and 4-methoxybenzyl protective groups have been attached to the amino acid 5-hydroxy-L-norvaline. The resulting glycosylated building blocks were used in Fmoc solid-phase synthesis of glycopeptides related to a fragment from type II collagen which is immunodominant in a mouse model for rheumatoid arthritis. The protective groups used for the carbohydrate moieties were completely removed during acid catalyzed cleavage of the glycopeptides from the solid phase under conditions which left the O-glycosidic bonds intact.

Preparation of a glycopeptide analogue of type II collagen - Use of acid labile protective groups for carbohydrate moieties in solid phase synthesis of O-linked glycopeptides

A glycopeptide analogue of the immunodeficient T cell epitope on type II collagen has been prepared by solid phase synthesis. Preparation of a glycosylated amino acid from two monosaccharide units that carried silyl and isopropylidene protective groups and Fmoc 5-hydroxynorvaline was essential for the synthesis. After assembly of the glycopeptide the carbohydrate protective groups were removed simultaneously with acid catalyzed cleavage from the solid phase.