(1E,5Z)-(3S,10S)-11-(tert-butyl-dimethylsilanyloxy)-2,6,10-trimethyl-1-(2-methylthiazol-4-yl)-undeca-1,5-dien-3-ol

Base Information

Chemical Name:(1E,5Z)-(3S,10S)-11-(tert-butyl-dimethylsilanyloxy)-2,6,10-trimethyl-1-(2-methylthiazol-4-yl)-undeca-1,5-dien-3-ol
CAS No.:853023-14-0
Molecular Formula:C₂₄H₄₃NO₂SSi
Molecular Weight:437.762
Hs Code.:

Synonyms:(1E,5Z)-(3S,10S)-11-(tert-butyl-dimethylsilanyloxy)-2,6,10-trimethyl-1-(2-methylthiazol-4-yl)-undeca-1,5-dien-3-ol

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Chemical Property of (1E,5Z)-(3S,10S)-11-(tert-butyl-dimethylsilanyloxy)-2,6,10-trimethyl-1-(2-methylthiazol-4-yl)-undeca-1,5-dien-3-ol

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Technology Process of (1E,5Z)-(3S,10S)-11-(tert-butyl-dimethylsilanyloxy)-2,6,10-trimethyl-1-(2-methylthiazol-4-yl)-undeca-1,5-dien-3-ol

There total 1 articles about (1E,5Z)-(3S,10S)-11-(tert-butyl-dimethylsilanyloxy)-2,6,10-trimethyl-1-(2-methylthiazol-4-yl)-undeca-1,5-dien-3-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:

: C₂₆H₄₅NO₆S₂Si

: 591-51-5
phenyllithium

: 853023-14-0
(1E,5Z)-(3S,10S)-11-(tert-butyl-dimethylsilanyloxy)-2,6,10-trimethyl-1-(2-methylthiazol-4-yl)-undeca-1,5-dien-3-ol

: 1209462-27-0
benzoic acid (Z)-(1S,8S)-9-(tert-butyl-dimethylsilanyloxy)-4,8-dimethyl-1-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]non-3-enyl ester

Guidance literature:: In tetrahydrofuran; dibutyl ether; at -78 ℃; for 3h; Inert atmosphere;
DOI:10.1002/chem.200901567

Reference yield: 85.0%

: 853023-14-0
(1E,5Z)-(3S,10S)-11-(tert-butyl-dimethylsilanyloxy)-2,6,10-trimethyl-1-(2-methylthiazol-4-yl)-undeca-1,5-dien-3-ol

: 69739-34-0
t-butyldimethylsiyl triflate

: 210690-85-0
(2S,6Z,9S,10E)-1,9-Bis[(1,1-dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-diene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1002/anie.200901740

Reference yield:

: 853023-14-0
(1E,5Z)-(3S,10S)-11-(tert-butyl-dimethylsilanyloxy)-2,6,10-trimethyl-1-(2-methylthiazol-4-yl)-undeca-1,5-dien-3-ol

: 189453-10-9
epothilone D

Guidance literature:: Multi-step reaction with 5 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

2: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 2.5 h / 0 °C

3: triethylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 1 h / 0 °C / Inert atmosphere

4: lithium iodide; chromium dichloride / tetrahydrofuran / 3.33 h / 20 °C / Inert atmosphere

5: trifluoroacetic acid / dichloromethane / 1.5 h / 0 °C

With chromium dichloride; dmap; (1S)-10-camphorsulfonic acid; sulfur trioxide pyridine complex; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium iodide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo401355r