{(2R,4S,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetic acid methyl ester

Base Information

Chemical Name:{(2R,4S,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetic acid methyl ester
CAS No.:477200-78-5
Molecular Formula:C₂₃H₃₈O₄SSi
Molecular Weight:438.704
Hs Code.:

Synonyms:{(2R,4S,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetic acid methyl ester

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Chemical Property of {(2R,4S,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetic acid methyl ester

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Technology Process of {(2R,4S,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetic acid methyl ester

There total 10 articles about {(2R,4S,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetic acid methyl 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: 87.0%

: 108-98-5
thiophenol

: {(R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-ethoxy-tetrahydro-pyran-4-yl}-acetic acid methyl ester

: {(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetic acid methyl ester

: 477200-78-5
{(2R,4S,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetic acid methyl ester

Guidance literature:: With magnesium bromide; In diethyl ether; at 20 ℃; for 2h;
DOI:10.1021/jo020537q

Reference yield:

: 112897-05-9
(5R,4R)-6-tert-butyldimethylsilyloxy-4-hydroxy-5-methylhex-1-ene

: 477200-78-5
{(2R,4S,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / N-iodosuccinimide / CH₂Cl₂ / 15 h / -23 - 0 °C

2.1: 97 percent / OsO₄; sodium periodate / tetrahydrofuran; H₂O; propan-2-ol / 15 h

3.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.67 h / -78 °C

3.2: 65 percent / tetrahydrofuran; toluene / 0.92 h / -78 °C

4.1: 86 percent / tri-n-butylstannane; azobisisobutyronitrile / toluene / 2 h / 80 °C

5.1: 87 percent / MgBr₂*OEt₂ / diethyl ether / 2 h / 20 °C

With sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; isopropyl alcohol; toluene; 3.2: Wadsworth-Emmons condensation;
DOI:10.1021/jo020537q

Reference yield:

: 197771-08-7
(3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(1-ethoxy-2-iodo-ethoxy)-4-methyl-pentanal

: 477200-78-5
{(2R,4S,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.67 h / -78 °C

1.2: 65 percent / tetrahydrofuran; toluene / 0.92 h / -78 °C

2.1: 86 percent / tri-n-butylstannane; azobisisobutyronitrile / toluene / 2 h / 80 °C

3.1: 87 percent / MgBr₂*OEt₂ / diethyl ether / 2 h / 20 °C

With 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; magnesium bromide; In tetrahydrofuran; diethyl ether; toluene; 1.2: Wadsworth-Emmons condensation;
DOI:10.1021/jo020537q