55287-65-5

Upstream product

• 117253-11-9 2-(trimethylsilyl)ethyl 2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside 
• 126257-35-0 2-(trimethylsilyl)ethyl 2-O-benzyl-β-D-glucopyranoside 
• 29741-67-1 1,3,4,6-tetra-O-acetyl-2-O-benzyl-β-D-glucopyranoside 
• 29741-69-3 3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide 
• 126257-36-1 2-(trimethylsilyl)ethyl 3,4,6-tri-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

• 173314-32-4 decyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside 
• 173314-33-5 decyl O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-(1<*>2)-3,4,6-tri-O-acetyl-α-D-glucopyranoside 
• 173314-36-8 decyl O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-(1<*>2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1<*>2)-3,4,6-tri-O-acetyl-α-D-glucopyranoside 
• 173314-38-0 decyl O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-(1<*>2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1<*>2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1<*>2)-3,4,6-tri-O-acetyl-α-D-glucopyranoside 
• 178757-74-9 Acetic acid (2S,3R,4S,5R,6R)-2,5-diacetoxy-6-acetoxymethyl-3-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 178757-76-1 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl 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

2-(Trimethylsilyl)ethyl Glycosides. Transformation into Glycopyranosyl Chlorides

2-(Trimethylsilyl)ethyl (TMSET) glycosides were transformed in high yields into the corresponding 1-chloro sugars by treatment with 1,1-dichloromethyl methyl ether/zinc chloride.With acetyl, benzoyl, and benzyl protection of the 2-postion, the α-glycopyranosyl chloride was the major product, whereas with the 2-phthalimido sugar 13, the β-chloride 21 was obtained.The fully benzylated TMSET glucopyranoside 1 gave the α-chloro sugar 22 carrying a 6-O-formyl group whereas the partially benzylated sugars 16 and 17 gave the chloro sugars with all protecting groups intact.