(1R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadec-3-yn-1-ol

Base Information

Chemical Name:(1R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadec-3-yn-1-ol
CAS No.:619315-57-0
Molecular Formula:C₃₈H₅₈O₄Si
Molecular Weight:606.962
Hs Code.:

Synonyms:(1R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadec-3-yn-1-ol

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Chemical Property of (1R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadec-3-yn-1-ol

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Technology Process of (1R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadec-3-yn-1-ol

There total 4 articles about (1R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadec-3-yn-1-ol 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: 88.0%

: 74134-79-5,212375-57-0
(4R)-2,2-dimethyl-4-[(2R)-oxiran-2-yl]-1,3-dioxolane

: 619315-55-8
tert-butyl-(1-dodecyl-prop-2-ynyloxy)-diphenyl-silane

: 619315-57-0
(1R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadec-3-yn-1-ol

Guidance literature:: tert-butyl-(1-dodecyl-prop-2-ynyloxy)-diphenyl-silane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(4R)-2,2-dimethyl-4-[(2R)-oxiran-2-yl]-1,3-dioxolane; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1016/S0040-4020(03)01134-7

Reference yield:

: 17746-06-4
n-tridecanoyl chloride

: 619315-57-0
(1R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadec-3-yn-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / AlCl₃ / CH₂Cl₂ / 2 h / 0 °C

2.1: 86 percent / (S)-Alpine borane / 16 h / 0 - 20 °C

3.1: 75 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

4.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / Heating

5.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: BF₃*OEt₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.3: 88 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With dmap; n-butyllithium; aluminium trichloride; (S)-alpine borane; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/S0040-4020(03)01134-7

Reference yield:

: 488808-07-7
(S)-pentadec-1-yn-3-ol

: 619315-57-0
(1R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadec-3-yn-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / Heating

2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: BF₃*OEt₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.3: 88 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/S0040-4020(03)01134-7