155020-86-3

Upstream product

• 100-39-0 benzyl bromide 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 155020-83-0 methyl (6R)-2,3,4-tri-O-benzyl-6-(2-thiazolyl)-α-D-mannopyranoside 
• 40653-17-6 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-formyl-α-D-mannopyranoside 
• 40653-16-5 methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside 
• 122588-56-1 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran 

Relevant academic research and scientific papers

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.

Synthesis of D-glycero-D-manno-heptose 1,7-bisphosphate (HBP) featuring a β-stereoselective bis-phosphorylation

D-glycero-D-manno-Heptose 1,7-bisphosphate (HBP) plays a unique role in bacteriology. We describe in this study a very efficient synthesis of HBP, featuring a highly 6-D-selective construction of the heptose scaffold as well as a double phosphorylation st

General Homologation Strategy for Synthesis of l -glycero- and d -glycero-Heptopyranoses

A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed α-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

Diastereoselectivity in the synthesis of D-glycero-D-aldoheptoses by 2-trimethylsilylthiazole homologation from hexodialdo-1,5-pyranose derivatives

An exploration of the synthesis of D-glycero-D-altro-heptose, a constitutent of O antigen chains in lipopolysaccharides from Campylobacter jejuni serotypes O:23 and O:36 led to a study of the 2-trimethylsilylthiazole homologation procedure for heptose syn