(3S,5R,7S,9S,11S,15R)-7-benzyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-en-1-ol

Base Information

Chemical Name:(3S,5R,7S,9S,11S,15R)-7-benzyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-en-1-ol
CAS No.:884345-39-5
Molecular Formula:C₄₁H₇₂O₉Si₂
Molecular Weight:765.188
Hs Code.:

(3S,5R,7S,9S,11S,15R)-7-benzyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-en-1-ol

Synonyms:(3S,5R,7S,9S,11S,15R)-7-benzyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-en-1-ol

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Chemical Property of (3S,5R,7S,9S,11S,15R)-7-benzyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-en-1-ol

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Technology Process of (3S,5R,7S,9S,11S,15R)-7-benzyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-en-1-ol

There total 20 articles about (3S,5R,7S,9S,11S,15R)-7-benzyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-en-1-ol 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: 85.0%

: 884345-38-4
(3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-ene

: 884345-39-5
(3S,5R,7S,9S,11S,15R)-7-benzyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-en-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/j.tetlet.2006.01.097

Reference yield:

: 884345-36-2
(S)-4-Benzyloxy-1-{(2S,6R)-4-[2-(tert-butyl-dimethyl-silanyloxy)-eth-(Z)-ylidene]-6-vinyl-tetrahydro-pyran-2-yl}-5-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3,3-dimethyl-pentan-2-one

: 884345-39-5
(3S,5R,7S,9S,11S,15R)-7-benzyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 58 percent / PPTS / methanol

2: 79 percent / iPr₂NEt / CH₂Cl₂ / 20 °C

3: 85 percent / nBu₄NF / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tetlet.2006.01.097

Reference yield:

: (E)-(2S,10R)-2-Benzyloxy-8-[2-(tert-butyl-dimethyl-silanyloxy)-eth-(Z)-ylidene]-1-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-10,11-dihydroxy-3,3-dimethyl-undec-5-en-4-one

: 884345-39-5
(3S,5R,7S,9S,11S,15R)-7-benzyloxy-13-[(Z)-2-(2-trimethylsilylethoxymethoxy)ethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxymethoxy)heptadec-16-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: t-BuOK / tetrahydrofuran / 0.25 h / 20 °C

2: Dess-Martin periodinane

3: t-BuLi

4: 58 percent / PPTS / methanol

5: 79 percent / iPr₂NEt / CH₂Cl₂ / 20 °C

6: 85 percent / nBu₄NF / tetrahydrofuran / 20 °C

With potassium tert-butylate; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 2: Dess-Martin oxidation / 3: Wittig condensation;
DOI:10.1016/j.tetlet.2006.01.097