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

Base Information

Chemical Name:(E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione
CAS No.:226940-49-4
Molecular Formula:C₅₇H₈₁NO₆SSi₂
Molecular Weight:964.51
Hs Code.:

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

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

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

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

There total 4 articles about (E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-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:

: C₆₄H₈₄Cl₃NO₈SSi₂

: 226940-49-4
(E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione

Guidance literature:: With dmap; In toluene; at 75 ℃; for 1h; Yield given;
DOI:10.1039/a809954e

Reference yield:

: 252986-91-7
(12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

: 226940-49-4
(E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N / tetrahydrofuran / 1 h / 0 °C

2: 4.7 g / DMAP / tetrahydrofuran; toluene / 1 h / 75 °C

With dmap; triethylamine; In tetrahydrofuran; toluene; 1: Acylation / 2: Cyclization;
DOI:10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B

Reference yield:

: 301652-21-1
(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienal

: 226940-49-4
(E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 4.24 g / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 2 h / 25 °C

2: 2.30 g / TBAF / tetrahydrofuran / 10 h / 0 - 25 °C

3: Et₃N / tetrahydrofuran / 1 h / 0 °C

4: 4.7 g / DMAP / tetrahydrofuran; toluene / 1 h / 75 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; water; toluene; tert-butyl alcohol; 1: Oxidation / 2: Silyl ether cleavage / 3: Acylation / 4: Cyclization;
DOI:10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B