(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid 2-trimethylsilanyl-ethyl ester

Base Information

Chemical Name:(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid 2-trimethylsilanyl-ethyl ester
CAS No.:611168-53-7
Molecular Formula:C₄₄H₈₂O₆Si₃
Molecular Weight:791.388
Hs Code.:

(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid 2-trimethylsilanyl-ethyl ester

Synonyms:(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid 2-trimethylsilanyl-ethyl ester

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Chemical Property of (3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of (3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid 2-trimethylsilanyl-ethyl ester

There total 14 articles about (3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid 2-trimethylsilanyl-ethyl ester 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: 73.0%

: 611168-53-7
(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:

Reference yield:

: 2916-68-9
2-(Trimethylsilyl)ethanol

: (3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid

: 611168-53-7
(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 25 ℃; for 12h;
DOI:10.1002/anie.200351819

Reference yield:

: 106-25-2
Nerol

: 611168-53-7
(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-1-methyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: (S,S)-2-nBu-4,5-(CONMe)2-1,3,2-dioxaborolan; Et₂Zn / 1,2-dimethoxy-ethane

2.1: 100 percent / NaH / dimethylformamide / 12 h / 0 - 25 °C

3.1: O₃ / CH₂Cl₂; methanol / -78 °C

3.2: 83 percent / NaBH₄ / CH₂Cl₂; methanol / 1 h / -78 - 25 °C

4.1: Et₃N / CH₂Cl₂ / 1 h / 25 °C

5.1: NaI / acetone / 12 h / 25 °C

6.1: LDA / tetrahydrofuran / 6 h / 0 °C

6.2: 87 percent / tetrahydrofuran / 14 h / -98 - -10 °C

7.1: MeI / 3 h / Heating

7.2: 91 percent / 3N HCl / pentane / 3 h / 25 °C

8.1: LDA / tetrahydrofuran; diethyl ether / 1.5 h / -78 - -40 °C

8.2: 80 percent / tetrahydrofuran; diethyl ether / 0.08 h / -78 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

10.1: HF; pyridine / tetrahydrofuran / 8 h / 0 °C

11.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

12.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 1 h / 25 °C

13.1: EDC; DMAP / dimethylformamide / 12 h / 25 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; (S,S)-2-nBu-4,5-(CONMe)2-1,3,2-dioxaborolan; hydrogen fluoride; diethylzinc; sodium hydride; ozone; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; sodium iodide; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 11.1: Swern oxidation;
DOI:10.1002/anie.200351819