(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3,7-bis-(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one

Base Information

Chemical Name:(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3,7-bis-(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one
CAS No.:396092-60-7
Molecular Formula:C₆₆H₁₀₅NO₈SSi₃
Molecular Weight:1156.88
Hs Code.:

(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3,7-bis-(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one

Synonyms:(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3,7-bis-(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one

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Chemical Property of (3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3,7-bis-(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one

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Technology Process of (3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3,7-bis-(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one

There total 31 articles about (3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3,7-bis-(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-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: 99.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 396092-46-9
(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3-tert-butyldimethylsilyloxy-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one

: 396092-60-7
(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3,7-bis-(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one

Guidance literature:: DOI:10.1016/S0040-4039(01)01795-6

Reference yield:

: 396092-19-6
(2S)-1-tert-butyldimethylsilyloxy-5-methyl-4-(phenylsulfonyl)hex-5-en-2-ol

: 396092-60-7
(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3,7-bis-(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one

Guidance literature:: Multi-step reaction with 15 steps

1.1: 78 percent / i-Pr₂EtN

2.1: Bu₃SnH; AIBN

2.2: SnBr₄ / -78 °C

3.1: 80 percent / pyridine

4.1: 59 percent / Bu₃SnH; AIBN

5.1: 91 percent / DDQ

6.1: 97 percent / Bu₄NF

7.1: Dess-Martin periodinane

8.1: 99 percent / Dess-Martin periodinane

9.1: 74 percent / n-BuLi

10.1: DIBAL-H

11.1: Dess-Martin periodinane

12.1: 67 percent / Li(i-Pr)2N / -78 °C

With pyridine; n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; 8.1: Dess-Martin oxidation / 10.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4039(01)01795-6

Reference yield:

: 396092-18-5
(2S)-5-methyl-4-(phenylsulfonyl)hex-5-ene-1,2-diol

: 396092-60-7
(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3,7-bis-(tert-butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one

Guidance literature:: Multi-step reaction with 16 steps

1.1: imid.

2.1: 78 percent / i-Pr₂EtN

3.1: Bu₃SnH; AIBN

3.2: SnBr₄ / -78 °C

4.1: 80 percent / pyridine

5.1: 59 percent / Bu₃SnH; AIBN

6.1: 91 percent / DDQ

7.1: 97 percent / Bu₄NF

8.1: Dess-Martin periodinane

9.1: 99 percent / Dess-Martin periodinane

10.1: 74 percent / n-BuLi

11.1: DIBAL-H

12.1: Dess-Martin periodinane

13.1: 67 percent / Li(i-Pr)2N / -78 °C

With pyridine; 1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; 9.1: Dess-Martin oxidation / 11.1: Dess-Martin oxidation / 14.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4039(01)01795-6