tert-Butyl-[(E)-(2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-enyloxy]-diphenyl-silane

Base Information

Chemical Name:tert-Butyl-[(E)-(2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-enyloxy]-diphenyl-silane
CAS No.:136262-69-6
Molecular Formula:C₃₆H₅₆O₅Si
Molecular Weight:596.923
Hs Code.:

Synonyms:tert-Butyl-[(E)-(2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-enyloxy]-diphenyl-silane

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Chemical Property of tert-Butyl-[(E)-(2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-enyloxy]-diphenyl-silane

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Technology Process of tert-Butyl-[(E)-(2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-enyloxy]-diphenyl-silane

There total 18 articles about tert-Butyl-[(E)-(2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-enyloxy]-diphenyl-silane 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: 87.0%

: 136262-68-5
(E)-(4S,5R,6S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-4,8-dimethyl-2-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-2-en-5-ol

: 77-78-1
dimethyl sulfate

: 136262-69-6
tert-Butyl-[(E)-(2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-enyloxy]-diphenyl-silane

Guidance literature:: With sodium hydride; In tetrahydrofuran;
DOI:10.1021/jo00019a004

Reference yield:

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

: 136262-69-6
tert-Butyl-[(E)-(2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-enyloxy]-diphenyl-silane

Guidance literature:: Multi-step reaction with 17 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

15: 87 percent / HOAc / tetrahydrofuran; H₂O

16: 91 percent / PPTS / acetone

17: 87 percent / NaH / tetrahydrofuran

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; zinc(II) tetrahydroborate; L-(+)-diisopropyl tartrate; impramine; iodine; pyridinium p-toluenesulfonate; 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; acetone; toluene;
DOI:10.1021/jo00019a004

Reference yield:

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

: 136262-69-6
tert-Butyl-[(E)-(2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-enyloxy]-diphenyl-silane

Guidance literature:: Multi-step reaction with 14 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

12: 87 percent / HOAc / tetrahydrofuran; H₂O

13: 91 percent / PPTS / acetone

14: 87 percent / NaH / tetrahydrofuran

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