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

Base Information

Chemical Name:Benzoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl ester
CAS No.:94958-31-3
Molecular Formula:C₂₁H₃₄O₆Si
Molecular Weight:410.583
Hs Code.:

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

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Chemical Property of Benzoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl ester

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

: (2R,4aR,6S,7R,8S,8aR)-6,8-Dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / NBS, AlBN / benzene / 25 °C

2: 1.) n-Bu₃SnH, AIBN; 2.) imidazole / 1.) PhH, 80 deg C; 2.) DMF, 25 deg C

With 1H-imidazole; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene;
DOI:10.1021/ja00292a038

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: Benzoic acid (2S,3S,4S,5R,6S)-2-bromomethyl-5-hydroxy-4,6-dimethoxy-tetrahydro-pyran-3-yl ester

: 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

Guidance literature:: With 1H-imidazole; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; Yield given. Multistep reaction; 1.) PhH, 80 deg C; 2.) DMF, 25 deg C;
DOI:10.1021/ja00292a038

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