(2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester

Base Information

Chemical Name:(2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester
CAS No.:869732-32-1
Molecular Formula:C₄₅H₇₁BrO₉Si
Molecular Weight:864.043
Hs Code.:

(2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester

Synonyms:(2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester

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Chemical Property of (2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester

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Technology Process of (2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester

There total 42 articles about (2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester 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: 87.0%

: 869732-18-3
(2E,6S,7S,8E,10S,11R,12S,14R)-ethyl 15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-hydroxy-11-(methoxymethoxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,8-dienoate

: 69739-34-0
t-butyldimethylsiyl triflate

: 869732-32-1
(2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ja055384d

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 869732-32-1
(2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / 1H-imidazole / dimethylformamide / 0 - 20 °C

2.1: DIBAL-H / toluene / 2 h / -78 °C

3.1: 19.8 g / benzene / 2 h / Heating

4.1: 95 percent / 4 Angstroem molecular sieves; Proton-Sponge / CH₂Cl₂ / 3 h / 20 °C

5.1: 99 percent / HCl / methanol / 1 h / 20 °C

6.1: 99 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 4 h / 20 °C

7.1: Cp₂ZrHCl / toluene / 6 h / 50 °C

7.2: ZnMe₂ / toluene / -65 - 0 °C

7.3: 55 percent / toluene / 1 h / 0 °C

8.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; Schwartz's reagent; oxalyl dichloride; 4 A molecular sieve; Proton-Sponge; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 6.1: Swern oxidation;
DOI:10.1021/ja055384d