(Z)-(2S,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-5,11-bis-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-2,8,10-trimethyl-undec-6-enal

Base Information

Chemical Name:(Z)-(2S,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-5,11-bis-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-2,8,10-trimethyl-undec-6-enal
CAS No.:1026877-90-6
Molecular Formula:C₅₄H₈₀O₆Si₃
Molecular Weight:909.482
Hs Code.:

(Z)-(2S,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-5,11-bis-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-2,8,10-trimethyl-undec-6-enal

Synonyms:(Z)-(2S,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-5,11-bis-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-2,8,10-trimethyl-undec-6-enal

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Chemical Property of (Z)-(2S,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-5,11-bis-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-2,8,10-trimethyl-undec-6-enal

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Technology Process of (Z)-(2S,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-5,11-bis-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-2,8,10-trimethyl-undec-6-enal

There total 15 articles about (Z)-(2S,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-5,11-bis-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-2,8,10-trimethyl-undec-6-enal 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:

: 92817-88-4
(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

: 1026877-90-6
(Z)-(2S,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-5,11-bis-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-2,8,10-trimethyl-undec-6-enal

Guidance literature:: Multi-step reaction with 15 steps

1: 91 percent / diethyl ether / -78 °C

2: 89 percent / (i-Pr)2NEt / CH₂Cl₂ / -78 °C

3: 85 percent / Grubbs' catalyst / CH₂Cl₂ / Heating

4: Dibal-H / CH₂Cl₂ / -78 °C

5: NaBH₄ / methanol / 0 °C

6: pyridine / 25 °C

7: (i-Pr)2NEt / CH₂Cl₂ / 25 °C

8: 93 percent / Dibal-H / CH₂Cl₂ / -78 °C

9: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

10: diethyl ether / -78 °C

11: 93 percent / imidazole / CH₂Cl₂

12: 89 percent / OsO₄; NMO; NaIO₄ / acetone; H₂O

13: diethyl ether / -78 °C

14: 85 percent / 2,6-lutidine / -78 °C

15: OsO₄; NMO; NaIO₄ / acetone; H₂O

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; water; acetone; 9: Swern oxidation;
DOI:10.1021/ol034958l

Reference yield:

: 106357-24-8
(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

: 1026877-90-6
(Z)-(2S,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-5,11-bis-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-2,8,10-trimethyl-undec-6-enal

Guidance literature:: Multi-step reaction with 14 steps

1: 89 percent / (i-Pr)2NEt / CH₂Cl₂ / -78 °C

2: 85 percent / Grubbs' catalyst / CH₂Cl₂ / Heating

3: Dibal-H / CH₂Cl₂ / -78 °C

4: NaBH₄ / methanol / 0 °C

5: pyridine / 25 °C

6: (i-Pr)2NEt / CH₂Cl₂ / 25 °C

7: 93 percent / Dibal-H / CH₂Cl₂ / -78 °C

8: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

9: diethyl ether / -78 °C

10: 93 percent / imidazole / CH₂Cl₂

11: 89 percent / OsO₄; NMO; NaIO₄ / acetone; H₂O

12: diethyl ether / -78 °C

13: 85 percent / 2,6-lutidine / -78 °C

14: OsO₄; NMO; NaIO₄ / acetone; H₂O

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; water; acetone; 8: Swern oxidation;
DOI:10.1021/ol034958l

Reference yield:

: 468738-71-8
(1S,2S)-1-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-2-methylbut-3-enyl prop-2-enoate

: 1026877-90-6
(Z)-(2S,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-5,11-bis-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-2,8,10-trimethyl-undec-6-enal

Guidance literature:: Multi-step reaction with 13 steps

1: 85 percent / Grubbs' catalyst / CH₂Cl₂ / Heating

2: Dibal-H / CH₂Cl₂ / -78 °C

3: NaBH₄ / methanol / 0 °C

4: pyridine / 25 °C

5: (i-Pr)2NEt / CH₂Cl₂ / 25 °C

6: 93 percent / Dibal-H / CH₂Cl₂ / -78 °C

7: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

8: diethyl ether / -78 °C

9: 93 percent / imidazole / CH₂Cl₂

10: 89 percent / OsO₄; NMO; NaIO₄ / acetone; H₂O

11: diethyl ether / -78 °C

12: 85 percent / 2,6-lutidine / -78 °C

13: OsO₄; NMO; NaIO₄ / acetone; H₂O

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; water; acetone; 7: Swern oxidation;
DOI:10.1021/ol034958l