phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

Base Information

• Chemical Name: phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside
• CAS No.: 170451-44-2
• Molecular Formula: C₂₇H₄₆O₈SSi
• Molecular Weight: 558.809
• Mol file: 170451-44-2.mol

Synonyms:phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

Chemical Property of phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

There total 1 articles about phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

(2S,3R,4S,5R)-4-[(2S,3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-2-phenylsulfanyl-tetrahydro-pyran-3,5-diol + methyl iodide (74-88-4) → phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside (170451-44-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 1h;

DOI:10.1021/ja993487o

Reference yield: 95.0%

phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside (170451-44-2) → phenyl 3-O-(2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-1-thio-β-D-xylopyranoside (261374-43-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 48h;

DOI:10.1021/ja993487o

Reference yield:

phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside (170451-44-2) → (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-α-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]octadecane-3,11-dione

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / TBAF / tetrahydrofuran / 48 h

2: 96 percent / NaI; NaH / tetrahydrofuran / 0.5 h / 65 °C

3: 13 percent / NBS; 4A MS / acetonitrile

With N-Bromosuccinimide; tetrabutyl ammonium fluoride; sodium hydride; sodium iodide; In tetrahydrofuran; acetonitrile; 1: desilylation / 2: benzylation / 3: Nicolaou glycosidation;

DOI:10.1021/ja993487o

upstream raw materials:

methyl iodide

Downstream raw materials:

phenyl 3-O-(2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

(1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]octadecane-3,11-dione

phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside