(E)-(4S,7R,8S,9S,16S)-13-Benzyloxymethyl-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

Base Information

Chemical Name:(E)-(4S,7R,8S,9S,16S)-13-Benzyloxymethyl-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione
CAS No.:211801-61-5
Molecular Formula:C₄₆H₇₅NO₆SSi₂
Molecular Weight:826.342
Hs Code.:

(E)-(4S,7R,8S,9S,16S)-13-Benzyloxymethyl-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

Synonyms:(E)-(4S,7R,8S,9S,16S)-13-Benzyloxymethyl-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

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Chemical Property of (E)-(4S,7R,8S,9S,16S)-13-Benzyloxymethyl-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

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Technology Process of (E)-(4S,7R,8S,9S,16S)-13-Benzyloxymethyl-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

There total 2 articles about (E)-(4S,7R,8S,9S,16S)-13-Benzyloxymethyl-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione 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: 40.0%

: 100-39-0
benzyl bromide

: 209260-82-2
(4S,7R,8S,9S,16S,E)-4,8-bis(tert-butyldimethylsilyloxy)-13-(hydroxymethyl)-5,5,7,9-tetramethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)oxacyclohexadec-13-ene-2,6-dione

: 211801-61-5
(E)-(4S,7R,8S,9S,16S)-13-Benzyloxymethyl-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at -15 - 20 ℃; for 3.5h;
DOI:10.1016/S0040-4020(98)00352-4

Reference yield:

: 201136-77-8
(12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

: 211801-61-5
(E)-(4S,7R,8S,9S,16S)-13-Benzyloxymethyl-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) 4-dimethylaminopyridine / 1.) THF, 0 deg C, 1 h, 2.) THF, toluene, 75 deg C, 3 h

2: 69 percent / formic acid / diethyl ether / 1.) -10 deg C, 10 min, 2.) -5 deg C, 3 h

3: 40 percent / NaH, Bu₄NI / tetrahydrofuran / 3.5 h / -15 - 20 °C

With dmap; formic acid; 2,4,6-trichlorobenzoyl chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether;
DOI:10.1016/S0040-4020(98)00352-4