(1E,8E,10E)-(3R,4R,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one

Base Information

Chemical Name:(1E,8E,10E)-(3R,4R,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one
CAS No.:477200-96-7
Molecular Formula:C₄₆H₆₁IO₅SSi
Molecular Weight:881.043
Hs Code.:

(1E,8E,10E)-(3R,4R,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one

Synonyms:(1E,8E,10E)-(3R,4R,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one

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Chemical Property of (1E,8E,10E)-(3R,4R,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one

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Technology Process of (1E,8E,10E)-(3R,4R,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one

There total 24 articles about (1E,8E,10E)-(3R,4R,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one 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:

: 477200-85-4
(2E,4E)-(R)-6-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-2-methyl-hepta-2,4-dienal

: C₂₉H₄₈BIO₂

: (1E,8E,10E)-(3R,4R,7R,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one

: 477200-96-7
(1E,8E,10E)-(3R,4R,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one

Guidance literature:: (2E,4E)-(R)-6-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-2-methyl-hepta-2,4-dienal; C₂₉H₄₈BIO₂; In diethyl ether; at -10 ℃; for 3h;

With dihydrogen peroxide; In methanol; diethyl ether; water; at 0 - 20 ℃; for 1.16667h; pH=7.0;
DOI:10.1021/jo020537q

Reference yield:

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

: 477200-96-7
(1E,8E,10E)-(3R,4R,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one

Guidance literature:: Multi-step reaction with 13 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

7.1: 76 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

8.1: 93 percent / acetic acid / tetrahydrofuran; H₂O / 18 h / 20 °C

9.1: 71 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - -20 °C

10.1: 77 percent / tetrahydrofuran / 16 °C / Heating

11.1: 92 percent / diisobutylaluminum hydride / diethyl ether; various solvent(s) / 1 h / -78 °C

12.1: 90 percent / manganese dioxide / diethyl ether / 2 h / 20 °C

13.1: diethyl ether / 3 h / -10 °C

13.2: 226 mg / H₂O₂ / diethyl ether; methanol; H₂O / 1.17 h / 0 - 20 °C / pH 7.0

With dmap; manganese(IV) oxide; sodium tetrahydroborate; sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; calcium chloride; magnesium bromide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; isopropyl alcohol; toluene; 3.2: Wadsworth-Emmons condensation / 10.1: Wittig reaction;
DOI:10.1021/jo020537q

Reference yield:

: 197771-06-5
tert-Butyl-[(2R,3R)-3-(1-ethoxy-2-iodo-ethoxy)-2-methyl-hex-5-enyloxy]-dimethyl-silane

: 477200-96-7
(1E,8E,10E)-(3R,4R,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-7-hydroxy-1-iodo-3-methoxy-2,4,8-trimethyl-trideca-1,8,10-trien-5-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: 97 percent / OsO₄; sodium periodate / tetrahydrofuran; H₂O; propan-2-ol / 15 h

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

2.2: 65 percent / tetrahydrofuran; toluene / 0.92 h / -78 °C

3.1: 86 percent / tri-n-butylstannane; azobisisobutyronitrile / toluene / 2 h / 80 °C

4.1: 87 percent / MgBr₂*OEt₂ / diethyl ether / 2 h / 20 °C

5.1: 92 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / 4 h / 0 - 20 °C

6.1: 76 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

7.1: 93 percent / acetic acid / tetrahydrofuran; H₂O / 18 h / 20 °C

8.1: 71 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - -20 °C

9.1: 77 percent / tetrahydrofuran / 16 °C / Heating

10.1: 92 percent / diisobutylaluminum hydride / diethyl ether; various solvent(s) / 1 h / -78 °C

11.1: 90 percent / manganese dioxide / diethyl ether / 2 h / 20 °C

12.1: diethyl ether / 3 h / -10 °C

12.2: 226 mg / H₂O₂ / diethyl ether; methanol; H₂O / 1.17 h / 0 - 20 °C / pH 7.0

With dmap; manganese(IV) oxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; calcium chloride; magnesium bromide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; isopropyl alcohol; toluene; 2.2: Wadsworth-Emmons condensation / 9.1: Wittig reaction;
DOI:10.1021/jo020537q