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

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Chemical Name:2-{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-ethanol
CAS No.:477200-79-6
Molecular Formula:C₂₂H₃₈O₃SSi
Molecular Weight:410.693
Hs Code.:

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

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

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

There total 11 articles about 2-{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-ethanol 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: 92.0%

: 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

: 477200-79-6
2-{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-ethanol

Guidance literature:: With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; at 0 - 20 ℃; for 4h;
DOI:10.1021/jo020537q

Reference yield:

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

: 477200-79-6
2-{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-ethanol

Guidance literature:: Multi-step reaction with 6 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

6.1: 92 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / 4 h / 0 - 20 °C

With sodium tetrahydroborate; sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; calcium chloride; magnesium bromide; In tetrahydrofuran; diethyl ether; ethanol; 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

: 477200-79-6
2-{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-ethanol

Guidance literature:: Multi-step reaction with 4 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

4.1: 92 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / 4 h / 0 - 20 °C

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