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

Base Information

Chemical Name:(E)-(2S,3R,6R,7R,8S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-7,8-dimethoxy-2,4,6,10-tetramethyl-undec-4-ene-1,3-diol
CAS No.:136262-71-0
Molecular Formula:C₃₃H₅₂O₅Si
Molecular Weight:556.858
Hs Code.:

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

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

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

There total 17 articles about (E)-(2S,3R,6R,7R,8S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-7,8-dimethoxy-2,4,6,10-tetramethyl-undec-4-ene-1,3-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: 80.0%

: 136262-70-9
(E)-(2S,3R,6R,7R,8S,10S)-1-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-7,8-dimethoxy-2,4,6,10-tetramethyl-undec-4-en-3-ol

: 136262-71-0
(E)-(2S,3R,6R,7R,8S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-7,8-dimethoxy-2,4,6,10-tetramethyl-undec-4-ene-1,3-diol

Guidance literature:: With acetic acid; In tetrahydrofuran; water;
DOI:10.1021/jo00019a004

Reference yield:

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

: 136262-71-0
(E)-(2S,3R,6R,7R,8S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-7,8-dimethoxy-2,4,6,10-tetramethyl-undec-4-ene-1,3-diol

Guidance literature:: Multi-step reaction with 16 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: 81 percent / NaH / tetrahydrofuran

15: BF₃*OEt₂ / tetrahydrofuran / -78 °C

16: 80 percent / HOAc / tetrahydrofuran; H₂O

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

Reference yield:

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

: 136262-71-0
(E)-(2S,3R,6R,7R,8S,10S)-11-(tert-Butyl-diphenyl-silanyloxy)-7,8-dimethoxy-2,4,6,10-tetramethyl-undec-4-ene-1,3-diol

Guidance literature:: Multi-step reaction with 13 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: 81 percent / NaH / tetrahydrofuran

12: BF₃*OEt₂ / tetrahydrofuran / -78 °C

13: 80 percent / HOAc / tetrahydrofuran; H₂O

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