(2S,9S,E)-9-(4-methoxybenzyloxy)-11-(tert-butyldiphenylsilyloxy)-2,9-dimethylundec-5-ene-1,2-diol

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Chemical Name:(2S,9S,E)-9-(4-methoxybenzyloxy)-11-(tert-butyldiphenylsilyloxy)-2,9-dimethylundec-5-ene-1,2-diol
CAS No.:931113-59-6
Molecular Formula:C₃₇H₅₂O₅Si
Molecular Weight:604.902
Hs Code.:

Synonyms:(2S,9S,E)-9-(4-methoxybenzyloxy)-11-(tert-butyldiphenylsilyloxy)-2,9-dimethylundec-5-ene-1,2-diol

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Chemical Property of (2S,9S,E)-9-(4-methoxybenzyloxy)-11-(tert-butyldiphenylsilyloxy)-2,9-dimethylundec-5-ene-1,2-diol

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Technology Process of (2S,9S,E)-9-(4-methoxybenzyloxy)-11-(tert-butyldiphenylsilyloxy)-2,9-dimethylundec-5-ene-1,2-diol

There total 14 articles about (2S,9S,E)-9-(4-methoxybenzyloxy)-11-(tert-butyldiphenylsilyloxy)-2,9-dimethylundec-5-ene-1,2-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: 37.0%

: 931113-82-5
C₄₀H₅₆O₅Si

: 931113-59-6
(2S,9S,E)-9-(4-methoxybenzyloxy)-11-(tert-butyldiphenylsilyloxy)-2,9-dimethylundec-5-ene-1,2-diol

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; for 3h; Heating;
DOI:10.1021/jo062513f

Reference yield:

: 871840-51-6
tert-butyldimethyl((4-methylpent-4-en-1-yl)oxy)silane

: 931113-59-6
(2S,9S,E)-9-(4-methoxybenzyloxy)-11-(tert-butyldiphenylsilyloxy)-2,9-dimethylundec-5-ene-1,2-diol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 36.0 g / (DHQ)2PHAL; K₃[Fe(CN)6]; K₂CO₃ / K₂OsO₂(OH)4 / 2-methyl-propan-2-ol; H₂O / 48 h / 0 °C

2.1: PPTS / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 21.77 g / TBAF / tetrahydrofuran / 2 h / cooling

4.1: 59 percent / Ph₃P; DIAD / tetrahydrofuran / 24 h / 20 °C

5.1: 60 percent / MCPBA / CH₂Cl₂ / 16 h / 20 °C

6.1: 84 percent / KHMDS / 1,2-dimethoxy-ethane; toluene / 2.5 h / -78 - 20 °C

7.1: 90 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

8.1: 96 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂; H₂O / 3 h / 20 °C

9.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

9.2: 99 percent / tetrahydrofuran / 1 h / -78 °C

10.1: Hg(OAc)2 / tetrahydrofuran; H₂O / 1 h / cooling

10.2: 72 percent / NaBH₄ / tetrahydrofuran; H₂O / 2 h

11.1: 99 percent / imidazole; DMAP / dimethylformamide / 0.5 h

12.1: 37 percent / PPTS / methanol / 3 h / Heating

With pyridine; 1H-imidazole; dmap; Hydroquinone 1,4-phthalazinediyl diether; di-isopropyl azodicarboxylate; mercury(II) diacetate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 4.1: Mitsunobu reaction / 6.1: Julia-Kocienski coupling / 8.1: Dess-Martin oxidation / 9.2: Wittig olefination;
DOI:10.1021/jo062513f

Reference yield:

: 22508-64-1
4-methyl-4-penten-1-ol

: 931113-59-6
(2S,9S,E)-9-(4-methoxybenzyloxy)-11-(tert-butyldiphenylsilyloxy)-2,9-dimethylundec-5-ene-1,2-diol

Guidance literature:: Multi-step reaction with 13 steps

1.1: DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

2.1: 36.0 g / (DHQ)2PHAL; K₃[Fe(CN)6]; K₂CO₃ / K₂OsO₂(OH)4 / 2-methyl-propan-2-ol; H₂O / 48 h / 0 °C

3.1: PPTS / CH₂Cl₂ / 1.5 h / 20 °C

4.1: 21.77 g / TBAF / tetrahydrofuran / 2 h / cooling

5.1: 59 percent / Ph₃P; DIAD / tetrahydrofuran / 24 h / 20 °C

6.1: 60 percent / MCPBA / CH₂Cl₂ / 16 h / 20 °C

7.1: 84 percent / KHMDS / 1,2-dimethoxy-ethane; toluene / 2.5 h / -78 - 20 °C

8.1: 90 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

9.1: 96 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂; H₂O / 3 h / 20 °C

10.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

10.2: 99 percent / tetrahydrofuran / 1 h / -78 °C

11.1: Hg(OAc)2 / tetrahydrofuran; H₂O / 1 h / cooling

11.2: 72 percent / NaBH₄ / tetrahydrofuran; H₂O / 2 h

12.1: 99 percent / imidazole; DMAP / dimethylformamide / 0.5 h

13.1: 37 percent / PPTS / methanol / 3 h / Heating

With pyridine; 1H-imidazole; dmap; Hydroquinone 1,4-phthalazinediyl diether; di-isopropyl azodicarboxylate; mercury(II) diacetate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 5.1: Mitsunobu reaction / 7.1: Julia-Kocienski coupling / 9.1: Dess-Martin oxidation / 10.2: Wittig olefination;
DOI:10.1021/jo062513f