(E)-(2S,3R,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide

Base Information

Chemical Name:(E)-(2S,3R,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide
CAS No.:169898-15-1
Molecular Formula:C₂₅H₄₃NO₅Si
Molecular Weight:465.706
Hs Code.:

Synonyms:(E)-(2S,3R,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide

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Chemical Property of (E)-(2S,3R,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide

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Technology Process of (E)-(2S,3R,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide

There total 11 articles about (E)-(2S,3R,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide 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: 95.0%

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 169898-14-0
(S)-4-Benzyl-3-[(E)-(2S,3R,5S)-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoyl]-oxazolidin-2-one

: 169898-15-1
(E)-(2S,3R,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide

Guidance literature:: With trimethylaluminum; In tetrahydrofuran; hexane; at 0 - 20 ℃;
DOI:10.1021/jo034011x

Reference yield: 91.0%

: 169898-14-0
(S)-4-Benzyl-3-[(E)-(2S,3R,5S)-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoyl]-oxazolidin-2-one

: 1117-97-1
N,0-dimethylhydroxylamine

: 169898-15-1
(E)-(2S,3R,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide

Guidance literature:: With trimethylaluminum;
DOI:10.1016/0040-4039(95)01194-M

Reference yield:

: 102191-92-4
tert-butyldimethylsiloxyacetaldehyde

: 169898-15-1
(E)-(2S,3R,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 84 percent / benzene / 48 h / 0 - 20 °C

2.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 78 percent / tetrahydrofuran / 0.08 h

3.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH₂Cl₂ / 20 h / -20 °C

3.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

4.1: 76 percent / TfOH

5.1: DIBAL-H

6.1: dibutylboron triflate; diisopropylethylamine / CH₂Cl₂ / 0.25 h / 0 °C

6.2: CH₂Cl₂ / 3 h / -78 °C

6.3: 89 percent / sodium acetate; hydrogen peroxide / methanol; CH₂Cl₂; H₂O / 1.5 h / 0 °C

7.1: 95 percent / trimethylaluminum / hexane; tetrahydrofuran / 0 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; diisobutylaluminium hydride; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; benzene; 1.1: Wittig olefination;
DOI:10.1021/jo034011x