142270-28-8

Basic information

• Product Name: ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside
• Synonyms: ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside
• CAS NO: 142270-28-8
• Molecular Weight: 743.049
• Mol File: 142270-28-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside(142270-28-8)
• EPA Substance Registry System: ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside(142270-28-8)

Safety Data

• Hazardous Substances Data: 142270-28-8(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 142270-27-7 ethyl 2,3,4-tri-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside 
• 65-85-0 benzoic acid 
• 100-39-0 benzyl bromide 
• 142270-22-2 1,6,7-tri-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranose 
• 142270-23-3 ethyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside 
• 142270-21-1 methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside 
• 122588-51-6 methyl-2,3,4-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside 

Downstream Products

• 142270-31-3 2-(4-trifluoroacetamidophenyl)ethyl O-<6-O-benzoyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranosyl>-(1-3)-2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside 
• 158464-34-7 2-(4-trifluoroacetamidophenyl)ethyl O-(6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-tert-butyldimethylsilyl-L-glycero-α-D-manno-heptopyranosyl)-(1<*>3)-2,4,6,7-tetra-O-acetyl-L-glycero-α-D-manno-heptopyranoside 
• 142270-30-2 2-(4-trifluoroacetamidophenyl)ethyl O-<6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranosyl>-(1-3)-2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside 

Relevant articles and documents

Stereodirecting Effect of C5-Carboxylate Substituents on the Glycosylation Stereochemistry of 3-Deoxy- d - Manno -oct-2-ulosonic Acid (Kdo) Thioglycoside Donors: Stereoselective Synthesis of α- And β-Kdo Glycosides

The stereodirecting effect of C5-ester functions on the glycosylation stereoselectivity of 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) ethyl thioglycoside donors is presented. The coupling of 5-O-arylcarbonyl or acetyl protected Kdo thioglycosides with acceptors proceeds in an α-selective and high-yielding manner, leading to formation of α-linked Kdo glycosides products. On the other hand, the glycosylation stereoselectivity of the 5-O-2-quinolinecarbonyl (Quin) or 4-nitropicoloyl substituted Kdo thioglycoside donors is switchable: (1) The glycosylation of the 5-O-Quin carrying Kdo donors with primary glycosyl acceptors shows complete β-stereoselectivity, furnishing the corresponding β-glycosides in good-to-excellent yield. (2) The stereochemical outcome of the secondary acceptors with these Kdo donors is determined mainly by the stereoelectronic nature of the acceptor. Only or predominant α anomeric products are obtained when the Kdo donors couple with the disarmed or highly crowded secondary carbohydrate acceptors, while the selectivity may switch to predominant β in the glycosylation of the 5-O-4-nitropicoloyl carrying donor with more reactive secondary alcohols. The synthetic use of the newly developed Kdo donors 1c and 7b has been demonstrated by facile preparation of a structurally unique trisaccharide motif 19 which possesses both α- and β-Kdo glycosidic bonds.