(E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol

Base Information

Chemical Name:(E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol
CAS No.:753016-45-4
Molecular Formula:C₄₅H₆₀O₆Si
Molecular Weight:725.053
Hs Code.:

Synonyms:(E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol

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Chemical Property of (E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol

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Technology Process of (E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol

There total 19 articles about (E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol 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: 73.0%

: 753016-44-3
(E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one

: 753016-45-4
(E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol

Guidance literature:: (E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one; With diethyl methoxy borane; In tetrahydrofuran; methanol; at 20 ℃; for 0.25h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -78 ℃; for 48h;
DOI:10.1021/ol049219z

Reference yield:

: 157733-27-2
(E)-(3'-bromo-but-2'-enyloxymethyl)-benzene

: 753016-45-4
(E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 68 percent / PdCl₂[P(o-Tol)3]2 / tetrahydrofuran / 96 h / 20 °C

2.1: 96 percent / DIBAL / CH₂Cl₂; hexane / -78 - 45 °C

3.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

4.1: Sn(OTf)2; Et₃N / CH₂Cl₂ / 3 h / -78 °C

4.2: 77 percent / CH₂Cl₂ / 6 h / -78 °C

5.1: diethylmethoxyborane / tetrahydrofuran; methanol / 0.25 h / 20 °C

5.2: 73 percent / NaBH₄ / tetrahydrofuran; methanol / 48 h / -78 °C

With tin(II) trifluoromethanesulfonate; diethyl methoxy borane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; hexane; dichloromethane; 4.2: Paterson's stereoselective aldol reaction;
DOI:10.1021/ol049219z

Reference yield:

: 753016-41-0
(E)-(S)-6-Benzyloxy-2,4-dimethyl-hex-4-enal

: 753016-45-4
(E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / Sn(OTf)2; triethylamine

2: Et₂BOMe; NaBH₄

With sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; triethylamine;
DOI:10.1016/j.tetlet.2005.07.029