{(1S,2S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-1-vinyl-but-3-enyloxy}-triethyl-silane

Base Information

Chemical Name:{(1S,2S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-1-vinyl-but-3-enyloxy}-triethyl-silane
CAS No.:892557-77-6
Molecular Formula:C₃₃H₅₆O₃Si
Molecular Weight:528.891
Hs Code.:

Synonyms:{(1S,2S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-1-vinyl-but-3-enyloxy}-triethyl-silane

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Chemical Property of {(1S,2S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-1-vinyl-but-3-enyloxy}-triethyl-silane

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Technology Process of {(1S,2S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-1-vinyl-but-3-enyloxy}-triethyl-silane

There total 12 articles about {(1S,2S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-1-vinyl-but-3-enyloxy}-triethyl-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: 83.0%

: (2R,3S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-3-triethylsilanyloxy-pent-4-enal

: 1779-49-3
Methyltriphenylphosphonium bromide

: 892557-77-6
{(1S,2S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-1-vinyl-but-3-enyloxy}-triethyl-silane

Guidance literature:: Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; toluene; at 0 ℃; for 1h;

(2R,3S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-3-triethylsilanyloxy-pent-4-enal; In tetrahydrofuran; toluene; at 0 ℃; for 2h;
DOI:10.1021/ol060704z

Reference yield:

: 892557-73-2
(3R,4S)-3-Benzyloxy-tetradec-1-en-4-ol

: 892557-77-6
{(1S,2S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-1-vinyl-but-3-enyloxy}-triethyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1.1: 86 percent / NaH / tetrahydrofuran; dimethylformamide / 2.5 h / 0 - 20 °C

2.1: triethylamine / tetrahydrofuran / 1.17 h / -78 - 0 °C

3.1: 303 mg / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

4.1: TiCl₄; N,N-diisopropylethylamine / CH₂Cl₂ / 5 h / -78 - -45 °C

4.2: 77 percent / N-methyl-2-pyrrolidinone / CH₂Cl₂ / 4 h / -78 - -40 °C

5.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

6.1: 95 percent / lithium borohydride; MeOH / diethyl ether; tetrahydrofuran / 2 h / 0 °C

7.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 0 °C

8.1: potassium t-butoxide / tetrahydrofuran; toluene / 1 h / 0 °C

8.2: 83 percent / tetrahydrofuran; toluene / 2 h / 0 °C

With 2,6-dimethylpyridine; methanol; lithium borohydride; n-butyllithium; oxalyl dichloride; potassium tert-butylate; titanium tetrachloride; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 7.1: Swern oxidation / 8.2: Wittig reaction;
DOI:10.1021/ol060704z

Reference yield:

: 2-((S)-(R)-1-Oxiranyl-undecyloxy)-tetrahydro-pyran

: 892557-77-6
{(1S,2S)-2-[(S)-1-((R)-1-Benzyloxy-allyl)-undecyloxy]-1-vinyl-but-3-enyloxy}-triethyl-silane

Guidance literature:: Multi-step reaction with 11 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -15 °C

1.2: 96 percent / tetrahydrofuran; hexane / 2 h / -15 - 25 °C

2.1: NaH; tetrabutylammonium iodide / tetrahydrofuran / 0 - 20 °C

3.1: 3.573 g / MeOH; p-toluenesulfonic acid / CH₂Cl₂ / 0 - 20 °C

4.1: 86 percent / NaH / tetrahydrofuran; dimethylformamide / 2.5 h / 0 - 20 °C

5.1: triethylamine / tetrahydrofuran / 1.17 h / -78 - 0 °C

6.1: 303 mg / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

7.1: TiCl₄; N,N-diisopropylethylamine / CH₂Cl₂ / 5 h / -78 - -45 °C

7.2: 77 percent / N-methyl-2-pyrrolidinone / CH₂Cl₂ / 4 h / -78 - -40 °C

8.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

9.1: 95 percent / lithium borohydride; MeOH / diethyl ether; tetrahydrofuran / 2 h / 0 °C

10.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 0 °C

11.1: potassium t-butoxide / tetrahydrofuran; toluene / 1 h / 0 °C

11.2: 83 percent / tetrahydrofuran; toluene / 2 h / 0 °C

With 2,6-dimethylpyridine; methanol; lithium borohydride; n-butyllithium; oxalyl dichloride; potassium tert-butylate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 10.1: Swern oxidation / 11.2: Wittig reaction;
DOI:10.1021/ol060704z