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

Base Information

Chemical Name:(2E,6S,7S,8E,10S,11R,12S,14R)-ethyl 15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-hydroxy-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoate
CAS No.:869732-18-3
Molecular Formula:C₃₉H₅₇BrO₉
Molecular Weight:749.78
Hs Code.:

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

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

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

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

There total 39 articles about (2E,6S,7S,8E,10S,11R,12S,14R)-ethyl 15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-hydroxy-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoate 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: 66.0%

: 869732-11-6
(6S,2E)-ethyl 6-methoxy-2-methyl-7-oxohept-2-enoate

: 869732-10-5
1-(benzyloxy)-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-(methoxymethoxy)-2,6-dimethylnon-7-yn-1-yl)benzene

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

: 1601460-66-5
C₂₈H₃₉BrO₅

Guidance literature:: 1-(benzyloxy)-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-(methoxymethoxy)-2,6-dimethylnon-7-yn-1-yl)benzene; With Schwartz's reagent; In toluene; at 50 ℃; for 6h; Inert atmosphere;

With dimethyl zinc(II); In toluene; at -78 - 0 ℃; Inert atmosphere;

(6S,2E)-ethyl 6-methoxy-2-methyl-7-oxohept-2-enoate; In toluene; at 0 ℃; for 1h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2014.03.020

Reference yield: 55.0%

: 869732-11-6
(6S,2E)-ethyl 6-methoxy-2-methyl-7-oxohept-2-enoate

: 869732-10-5
1-(benzyloxy)-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-(methoxymethoxy)-2,6-dimethylnon-7-yn-1-yl)benzene

: 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

Guidance literature:: 1-(benzyloxy)-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-(methoxymethoxy)-2,6-dimethylnon-7-yn-1-yl)benzene; With Schwartz's reagent; In toluene; at 50 ℃; for 6h;

With dimethyl zinc(II); In toluene; at -65 - 0 ℃;

(6S,2E)-ethyl 6-methoxy-2-methyl-7-oxohept-2-enoate; In toluene; at 0 ℃; for 1h;
DOI:10.1021/ja055384d

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; 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