(R)-1-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-7-trimethylsilanyl-hept-6-yn-3-ol

Base Information

Chemical Name:(R)-1-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-7-trimethylsilanyl-hept-6-yn-3-ol
CAS No.:799296-76-7
Molecular Formula:C₃₈H₆₂O₄Si₃
Molecular Weight:667.164
Hs Code.:

(R)-1-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-7-trimethylsilanyl-hept-6-yn-3-ol

Synonyms:(R)-1-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-7-trimethylsilanyl-hept-6-yn-3-ol

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Chemical Property of (R)-1-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-7-trimethylsilanyl-hept-6-yn-3-ol

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Technology Process of (R)-1-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-7-trimethylsilanyl-hept-6-yn-3-ol

There total 6 articles about (R)-1-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-7-trimethylsilanyl-hept-6-yn-3-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: 65.0%

: 41423-29-4
4-iodo-1-butynyltrimethylsilane

: 799296-75-6
(R)-3-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

: 799296-76-7
(R)-1-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-7-trimethylsilanyl-hept-6-yn-3-ol

Guidance literature:: 4-iodo-1-butynyltrimethylsilane; With tert.-butyl lithium; In diethyl ether; hexane; at -78 - 20 ℃; for 0.75h;

With copper(l) iodide; In diethyl ether; hexane; at -78 ℃; for 0.0833333h;

(R)-3-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde; In diethyl ether; hexane; at -78 ℃; for 1h;
DOI:10.1021/ol048581a

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 799296-76-7
(R)-1-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-7-trimethylsilanyl-hept-6-yn-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

2.1: 86 percent / H₂ / Pd(OH)2/C / ethyl acetate / 12 h / 20 °C / 760 Torr

3.1: 83 percent / imidazole; DMAP / CH₂Cl₂ / 24 h / 20 °C

4.1: 73 percent / DMSO; (COCl)2 / CH₂Cl₂ / -78 - -35 °C

5.1: t-BuLi / diethyl ether; hexane / 0.75 h / -78 - 20 °C

5.2: CuI / diethyl ether; hexane / 0.08 h / -78 °C

5.3: 65 percent / diethyl ether; hexane / 1 h / -78 °C

With 1H-imidazole; dmap; oxalyl dichloride; hydrogen; tert.-butyl lithium; dimethyl sulfoxide; palladium dihydroxide; In diethyl ether; hexane; dichloromethane; ethyl acetate; 4.1: Swern oxidation;
DOI:10.1021/ol048581a

Reference yield:

: (2R,3R,5R)-2-((R)-3-Benzyloxy-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-ol

: 799296-76-7
(R)-1-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-7-trimethylsilanyl-hept-6-yn-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

2.1: 86 percent / H₂ / Pd(OH)2/C / ethyl acetate / 12 h / 20 °C / 760 Torr

3.1: 83 percent / imidazole; DMAP / CH₂Cl₂ / 24 h / 20 °C

4.1: 73 percent / DMSO; (COCl)2 / CH₂Cl₂ / -78 - -35 °C

5.1: t-BuLi / diethyl ether; hexane / 0.75 h / -78 - 20 °C

5.2: CuI / diethyl ether; hexane / 0.08 h / -78 °C

5.3: 65 percent / diethyl ether; hexane / 1 h / -78 °C

With 1H-imidazole; dmap; oxalyl dichloride; hydrogen; tert.-butyl lithium; dimethyl sulfoxide; palladium dihydroxide; In diethyl ether; hexane; dichloromethane; ethyl acetate; 4.1: Swern oxidation;
DOI:10.1021/ol048581a