(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid

Base Information

Chemical Name:(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid
CAS No.:869732-33-2
Molecular Formula:C₄₃H₆₇BrO₉Si
Molecular Weight:835.989
Hs Code.:

(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid

Synonyms:(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid

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Chemical Property of (2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid

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Technology Process of (2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid

There total 42 articles about (2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid 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: 94.0%

: 869732-32-1
(2E,6S,7S,8E,10S,11R,12S,14R)-ethyl 15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoate

: 869732-33-2
(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid

Guidance literature:: With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 20 ℃; for 48h; Inert atmosphere;
DOI:10.1016/j.tet.2014.03.020

Reference yield:

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

: 869732-33-2
(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid

Guidance literature:: Multi-step reaction with 9 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

9.1: aq. LiOH / tetrahydrofuran; methanol / 48 h

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