(E)-(2S,3R,6S,7R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6,10-tetramethyl-undec-4-ene-3,7-diol

Base Information

Chemical Name:(E)-(2S,3R,6S,7R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6,10-tetramethyl-undec-4-ene-3,7-diol
CAS No.:136262-66-3
Molecular Formula:C₃₈H₆₄O₅Si₂
Molecular Weight:657.094
Hs Code.:

Synonyms:(E)-(2S,3R,6S,7R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6,10-tetramethyl-undec-4-ene-3,7-diol

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Chemical Property of (E)-(2S,3R,6S,7R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6,10-tetramethyl-undec-4-ene-3,7-diol

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Technology Process of (E)-(2S,3R,6S,7R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6,10-tetramethyl-undec-4-ene-3,7-diol

There total 15 articles about (E)-(2S,3R,6S,7R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6,10-tetramethyl-undec-4-ene-3,7-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: 8.0%

: C₂H₃CuN^(1-)*CH₃Li*Li⁽¹⁺⁾

: 136262-64-1
(E)-(3R,4S,6S)-1-{(2S,3R)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-6-methyl-hept-1-en-3-ol

: (4E,6E)-(2S,3R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6,10-tetramethyl-undeca-4,6-dien-3-ol

: 136262-66-3
(E)-(2S,3R,6S,7R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6,10-tetramethyl-undec-4-ene-3,7-diol

Guidance literature:: In tetrahydrofuran; at 0 ℃; Yields of byproduct given;
DOI:10.1021/jo00019a004

Reference yield:

: 123444-68-8
(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

: 136262-66-3
(E)-(2S,3R,6S,7R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6,10-tetramethyl-undec-4-ene-3,7-diol

Guidance literature:: Multi-step reaction with 11 steps

2: DIBAH

3: L-(+)-DIPT, TBHP, TIP / -30 °C

4: Ph₃P, I₂, Im

5: n-BuLi / tetrahydrofuran / -78 deg C to room temp.

7: 1.) O₃, KOH / CH₂Cl₂

8: 78 percent

9: 80 percent / K₂CO₃ / 18-C-6 / toluene

10: Zn(BH₄)2 / diethyl ether / -45 °C

11: tetrahydrofuran / 0 °C

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; zinc(II) tetrahydroborate; L-(+)-diisopropyl tartrate; impramine; iodine; diisobutylaluminium hydride; isobutyltriphenylphosphonium bromide; potassium carbonate; ozone; triphenylphosphine; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1021/jo00019a004

Reference yield:

: 95514-04-8,129029-85-2,120346-83-0
(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

: 136262-66-3
(E)-(2S,3R,6S,7R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6,10-tetramethyl-undec-4-ene-3,7-diol

Guidance literature:: Multi-step reaction with 14 steps

1: Et₃N

2: NaI / dimethylsulfoxide

3: DIBAH / diethyl ether

5: DIBAH

6: L-(+)-DIPT, TBHP, TIP / -30 °C

7: Ph₃P, I₂, Im

8: n-BuLi / tetrahydrofuran / -78 deg C to room temp.

10: 1.) O₃, KOH / CH₂Cl₂

11: 78 percent

12: 80 percent / K₂CO₃ / 18-C-6 / toluene

13: Zn(BH₄)2 / diethyl ether / -45 °C

14: tetrahydrofuran / 0 °C

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; zinc(II) tetrahydroborate; L-(+)-diisopropyl tartrate; impramine; iodine; diisobutylaluminium hydride; isobutyltriphenylphosphonium bromide; potassium carbonate; ozone; triethylamine; triphenylphosphine; sodium iodide; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; toluene;
DOI:10.1021/jo00019a004