190248-99-8

Basic information

• Product Name: ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside
• Synonyms: ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside
• CAS NO: 190248-99-8
• Molecular Weight: 372.529
• Mol File: 190248-99-8.mol

Chemical Properties

• CAS DataBase Reference: ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside(190248-99-8)
• EPA Substance Registry System: ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside(190248-99-8)

Safety Data

• Hazardous Substances Data: 190248-99-8(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 810661-47-3 ethyl 3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside 
• 810661-46-2 ethyl 2,4-di-O-acetyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside 
• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 6696-41-9 alpha-L-fucose 
• 127501-41-1 ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 132799-10-1 ethyl 1-thio-α-L-fucopyranoside 
• 162467-81-4 Ethyl 2,4-di-O-acetyl-1-thio-β-L-fucopyranoside 
• 64913-16-2 L-fucose tetraacetate 
• 1054623-78-7 Acetic acid (3aR,4S,6R,7S,7aR)-2-ethoxy-6-ethylsulfanyl-2,4-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 810661-45-1 ethyl 2,4-di-O-acetyl-3-O-(imidazol-1-ylthiocarbonyl)-1-thio-β-L-fucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 190248-98-7 ethyl 2,4-di-O-benzyl-1-thio-β-L-fucopyranoside 
• 190248-97-6 (2R,3aR,4S,6R,7S,7aR)-7-Benzyloxy-6-ethylsulfanyl-4-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 

Downstream Products

• 190248-93-2 C₇₄H₉₁NO₁₇ 
• 884655-01-0 2-[2-(2-azidoethoxy)ethoxy]ethyl 3-O-benzyl-2-O-(2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl)-β-D-galactopyranoside cyclic [P(R)]-4,6-(2,2,2-trichloroethyl phosphate) 
• 144685-09-6 2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl bromide 

Relevant articles and documents

Synthesis of a phosphorylated disaccharide fragment of the O-specific polysaccharide of Vibrio cholerae O139, functionalized for conjugation

The title disaccharide, 2-(2-(2-[(2-ethoxy-3,4-dioxocyclobut-1-en-1-yl) amino]ethoxy}ethoxy}ethyl 2-O-(3,6-dideoxy-α-L-xylo-hexopyranosyl)-β- D-galactopyranoside cyclic 4,6-(potassium phosphate) (2), was synthesized from the two isomeric linker-equipped galactose acceptors 9 and 10, obtained by phosphorylation of 2-[2-(2-azidoethoxy)ethoxy]ethyl 3-O-benzyl-β-D- galactopyranoside (8). which were glycosylated with ethyl 2,4-di-O-benzyl-3,6- dideoxy-1-thio-β-L-xylo-hexopyranoside (12; Scheme). Mainly the fully protected α-(1 → 2)-linked products 13a and 14a were formed. Catalytic hydrogenolysis/hydrogenation effected global deprotection, thereby removing the chirality at the P-atom. and simultaneously converted the azido group in the linker to an amino group (→15). Final treatment with diethyl squarate (=3,4-diethoxycyclobut-3-ene-1,2-dione) gave target compound 2, amenable for conjugation to proteins.

A facile synthesis of armed and disarmed colitose thioglycosides

Ethyl 2,4-di-O-acetyl-3,6-dideoxy-1-thio-β-L-xylohexopyranoside (10) and ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xyl0-hexopyranoside (12) were synthesized in 60% and 55% overall yield, respectively. Starting from α-L-fucose, sequential peracetylation

Synthesis of colitose-containing oligosaccharide structures found in polysaccharides from Vibrio cholerae O139 synonym Bengal using thioglycoside donors

The syntheses of the two colitose-containing trisaccharides 8-methoxycarbonyloctyl (3,6-dideoxy- α-L-xylo-hexopyranosyl)-(1 → 2)-β-D-galactopyranosyl-(1 → 3)-2-acetamido-2-deoxy-β-D-glucopyranoside and 8-methoxycarbonyloctyl β-D-galactopyranosyl-(1 → 3)-[