157239-66-2

Upstream product

• 117606-53-8 phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 108-98-5 thiophenol 
• 3282-30-2 pivaloyl chloride 

Downstream Products

• 183875-05-0 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-((2R,4aR,6R,7R,8R,8aS)-7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 183875-09-4 C₅₈H₆₉N₃O₁₈S 
• 183875-06-1 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 183875-23-2 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester 
• 183875-24-3 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6R)-3-azido-5-hydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-3-yl ester 
• 183875-18-5 C₅₁H₇₃N₃O₁₅S 

Relevant academic research and scientific papers

Synthesis of D-galactopyranosides of trans-4-hydroxy-L-proline utilizing the sulfoxide glycosylation method

Phenyl 1-thio-β-D-galactopyranoside (1) was converted into two sulfoxide glycosyl donors: phenyl (2,3,4,6-tetra-O-benzyl)-1-thio-β-D-galactopyranoside S-oxide (3) and phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside S-oxide (5). These glycosyl donors were then each reacted with Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester (7). The glycosylation reactions were conducted at -70°C with triflic anhydride as promotor, in the presence of 2,6-di-tert-butyl-4-methylpyridine. In the case of the perbenzylated sulfoxide donor (3), the major product was Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzyl)- α-D-galactopyranosyl]-L-proline allyl ester (8α). In dichloromethane, the α-to-β ratio was 3:1 and in toluene this improved to 5:1, with a combined yield of 41%. In the case of the perpivaloylated sulfoxide donor (5), Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-pivaloyl )-β-D-galactopyranosyl]-L-proline allyl ester (9) was obtained as the sole glycoside product in 46% yield.

Sulfinyl hexose derivatives useful for glycosylation

Hexose derivatives are described which facilitate control over the stereochemistry of the glycosyl bond formed in the course of a solid phase glycosylation reaction. Methods for their use are also described.

Generalizing glycosylation: Synthesis of the blood group antigens Lea, Leb, and Le(x) using a standard set of reaction conditions

Because there are no general reaction conditions for any glycosylation method, biologically interesting oligosaccharides can only be made in a small number of laboratories in the world. To make carbohydrate synthesis accessible to nonspecialists, it is critical to have glycosylation methods that will work in a wide range of cases under a single set of conditions. The Lewis blood group antigens have attracted the attention of numerous synthetic carbohydrate groups because of their structural complexity. Although they have been synthesized many times, they have never been made using a single glycosylation method under one set of reaction conditions. In this paper, we show that the sulfoxide glycosylation method can be used to form all of the glycosidic linkages in the Lewis blood group antigens Lea (1), Leb (2), and Le(x) (3) stereoselectively under a uniform set of reaction conditions. This work highlights the flexibility of the sulfoxide method and demonstrates its utility for constructing families of related oligosaccharides.