((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: ((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane
• CAS No.: 412342-77-9
• Molecular Formula: C₃₁H₄₀O₂Si
• Molecular Weight: 472.743
• Mol file: 412342-77-9.mol

Synonyms:((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane

Chemical Property of ((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane

There total 1 articles about ((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-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: 92.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-hex-5-en-3-ol → ((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane (412342-77-9)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 20 ℃; for 3.5h;

DOI:10.1021/ol017266a

Reference yield:

((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane (412342-77-9) → (3S,4S,5R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexan-1-ol

Guidance literature:

((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane; With benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; at 0 - 20 ℃;

With sodium hydroxide; In methanol; at 0 ℃; for 2h; Further stages.;

DOI:10.1021/ol017266a

Reference yield:

((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane (412342-77-9) → (Z)-(2R,3S,4S,5S)-8-Iodo-1-(4-methoxy-benzyloxy)-2,4,7-trimethyl-5-triethylsilanyloxymethyl-oct-7-en-3-ol

Guidance literature:

Multi-step reaction with 8 steps

1.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 0 - 20 °C

1.2: 27.5percent H₂O₂; 2N NaOH / methanol / 2 h / 0 °C

2.1: PDC / dimethylformamide / 48 h / 20 °C

3.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

4.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

4.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

5.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

6.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

7.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

8.1: imidazole / dimethylformamide / 1.5 h / 0 °C

With 1H-imidazole; dipyridinium dichromate; lithium borohydride; Li(Pr-i)2; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol017266a

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

Downstream raw materials:

(4S,5S)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

(3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

(2S,3S,4S,5R)-2-((Z)-3-Iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexane-1,4-diol

(2S,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((Z)-3-iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanal