(E)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-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-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione
CAS No.:201136-78-9
Molecular Formula:C₅₂H₆₉NO₆SSi
Molecular Weight:864.274
Hs Code.:

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

There total 1 articles about (E)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-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:

: 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

: 201136-78-9
(E)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione

Guidance literature:: With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; Yield given. Multistep reaction; 1.) THF, 0 deg C, 1 h, 2.) THF, toluene, 75 deg C, 1 h;
DOI:10.1039/a705845d

Reference yield:

: 201136-78-9
(E)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione

: Benzoic acid (E)-(2S,9S,10S,11R,14S)-10,14-dihydroxy-9,11,13,13-tetramethyl-2-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-12,16-dioxo-oxacyclohexadec-4-en-5-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / camphorosulfonic acid / methanol; CH₂Cl₂ / 3 h / 0 - 25 °C

2: DMAP, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 30percent HF*pyridine / tetrahydrofuran / 24 h / 0 - 25 °C

With dmap; camphor-10-sulfonic acid; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1039/a705845d

Reference yield:

: 201136-78-9
(E)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione

: Benzoic acid (1S,3S,7S,10R,11S,12S,16S)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadec-16-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / 30percent HF*pyridine / tetrahydrofuran / 24 h / 0 - 25 °C

2: 76 percent / (+)-diethyl L-tartrate, Ti(O-i-Pr)4, t-BuOOH / 2 h / -30 °C

3: DMAP, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; diethyl (2R,3R)-tartrate; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1039/a705845d