173314-29-9

Upstream product

• 4551-15-9 phenylthiotrimethylsilane 
• 29741-67-1 1,3,4,6-tetra-O-acetyl-2-O-benzyl-β-D-glucopyranoside 
• 173314-28-8 phenyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α-D-glucopyranoside 

Downstream Products

• 181025-97-8 Acetic acid (2R,3S,4S,5R,6R)-5-benzyloxy-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 181025-99-0 Acetic acid (3aR,4R,6S,7R,7aS)-7-benzyloxy-6-chloro-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester 
• 181026-06-2 C₅₉H₈₄O₂₉ 
• 181026-02-8 6-[(2S,3R,4S,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-((3aR,4R,6R,7R,7aS)-4-acetoxymethyl-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester 
• 181025-98-9 Acetic acid (3aR,4R,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester 

Relevant academic research and scientific papers

Synthesis of a pentasaccharide fragmant of Polysaccharide II of Mycobacterium tuberculosis

Stereocontrolled, stepwise synthesis of decyl glycosides of α-(1 -->2)-linked di- to pentaglucosides (1-5) is described; these constitute fragments of Polysaccharide II of Mycobacterium tuberculosis.Phenyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-?-D-glucopyranoside (7) was used as the single key intermediate, obtained from 1,3,4,6-tetra-O-acetyl-2-O-benzyl-β-D-glucopyranose (6) and PhSSiMe3.Halogenolysis of 7 afforded the isolated β bromide (10) and β chloride (13).Solvolysis of 10 with decanol without heavy metal salts gave decyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside (14) in a highly stereoselective reaction, in high yield.Subsequent, iterative hydrogenolytic removal of the O-benzyl group and glycosylation with the β-chloride 13 under catalysis by silver salts afforded the protected di- to penta-saccharide glycosides 16, 19, 21, and 23, which were conventionally deblocked.Keywords: Pentasaccharide; Polysaccharide II; Mycobacterium tuberculosis