(3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxy)methoxyhexadecan-16-ol

Base Information

Chemical Name:(3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxy)methoxyhexadecan-16-ol
CAS No.:807365-88-4
Molecular Formula:C₆₆H₉₄O₉Si₃
Molecular Weight:1115.72
Hs Code.:

(3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxy)methoxyhexadecan-16-ol

Synonyms:(3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxy)methoxyhexadecan-16-ol

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Chemical Property of (3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxy)methoxyhexadecan-16-ol

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Technology Process of (3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxy)methoxyhexadecan-16-ol

There total 5 articles about (3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxy)methoxyhexadecan-16-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: 71.0%

: 807365-81-7
(3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-16-(4-methoxybenzyloxy)-3-(2-trimethylsilylethoxy)methoxyhexadecane

: 807365-88-4
(3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxy)methoxyhexadecan-16-ol

Guidance literature:: (3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-16-(4-methoxybenzyloxy)-3-(2-trimethylsilylethoxy)methoxyhexadecane; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

With pyridinium p-toluenesulfonate; trimethyl orthoformate; In methanol; Further stages.;
DOI:10.1016/j.tetlet.2004.09.124

Reference yield:

: 807365-58-8
(E)-(2S,10R)-2-Benzyloxy-1-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-8-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-10-hydroxy-11-(4-methoxy-benzyloxy)-3,3-dimethyl-undec-5-en-4-one

: 807365-88-4
(3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxy)methoxyhexadecan-16-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: tBuOK / tetrahydrofuran / 0.08 h / 20 °C

2.1: PPTS / methanol / 19 h / 20 °C

3.1: 85 percent / iPr₂NEt / CH₂Cl₂

4.1: DDQ / CH₂Cl₂

4.2: 71 percent / (MeO)3CH; PPTS / methanol

With potassium tert-butylate; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tetlet.2004.09.124

Reference yield:

: 807365-65-7
(S)-4-Benzyloxy-5-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-1-[(2S,6R)-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-3,3-dimethyl-pentan-2-one

: 807365-88-4
(3S,5R,7S,9S,11S,15R)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-13-[(Z)-2-tert-butyldiphenylsilyloxyethylidene]-5,9-epoxy-11,15-epoxy-8,8-dimethyl-9-methoxy-3-(2-trimethylsilylethoxy)methoxyhexadecan-16-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: PPTS / methanol / 19 h / 20 °C

2.1: 85 percent / iPr₂NEt / CH₂Cl₂

3.1: DDQ / CH₂Cl₂

3.2: 71 percent / (MeO)3CH; PPTS / methanol

With N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; pyridinium p-toluenesulfonate; In methanol; dichloromethane;
DOI:10.1016/j.tetlet.2004.09.124