(2R,3R,4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol
CAS No.:94958-15-3
Molecular Formula:C₁₉H₃₂O₄SSi
Molecular Weight:384.612
Hs Code.:

Synonyms:(2R,3R,4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

There total 1 articles about (2R,3R,4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol 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: 73.0%

: 4551-15-9
phenylthiotrimethylsilane

: 94958-31-3
Benzoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl ester

: 94958-15-3
(2R,3R,4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

: (2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: With tetra-(n-butyl)ammonium iodide; potassium carbonate; zinc(II) iodide; Yield given. Multistep reaction; 1.) ClCH₂CH₂Cl, 65 deg C, 2.5 h; 2.) MeOH, 0-25 deg C, 4.5 h;
DOI:10.1021/ja00292a038

Reference yield: 84.0%

: 94958-16-4
tert-Butyl-((2S,3R,4R,5S,6S)-2-fluoro-3,5-dimethoxy-6-methyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane

: 94958-15-3
(2R,3R,4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

: C₃₃H₆₀O₈SSi₂

Guidance literature:: With silver perchlorate; tin(ll) chloride; In diethyl ether; at -15 - 25 ℃; for 2h;
DOI:10.1021/ja00292a039

Reference yield:

: 94958-15-3
(2R,3R,4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

: Acetic acid (2R,3R,4R,5R,6R)-5-((2S,3R,4R,5S,6S)-4-acetoxy-3,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / SnCl₂, AgClO₄, 4AMS / diethyl ether / 2 h / -15 - 25 °C

2: n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

3: 96 percent / DMAP / CH₂Cl₂ / 0.03 h / 0 °C

With tetrabutyl ammonium fluoride; silver perchlorate; tin(ll) chloride; dmap; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00292a039