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

Base Information

• Chemical Name: (4S,5S)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one
• CAS No.: 412342-76-8
• Molecular Formula: C₂₄H₃₂O₃Si
• Molecular Weight: 396.602
• Mol file: 412342-76-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (4S,5S)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one 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%

(3S,4S,5R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexanoic acid (412342-78-0) → (4S,5S)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one (412342-76-8)

Guidance literature:

With hydrogen; 20percent Pd(OH)2/C; In methanol;

DOI:10.1021/ol017266a

Reference yield:

(2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-hex-5-en-3-ol → (4S,5S)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one (412342-76-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 92 percent / TfOH / CH₂Cl₂ / 3.5 h / 20 °C

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

2.2: 27.5percent H₂O₂; 2N NaOH / methanol / 2 h / 0 °C

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

4.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

With dipyridinium dichromate; trifluorormethanesulfonic acid; hydrogen; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol017266a

Reference yield:

((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane (412342-77-9) → (4S,5S)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one (412342-76-8)

Guidance literature:

Multi-step reaction with 3 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

With dipyridinium dichromate; hydrogen; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol017266a

upstream raw materials:

(4α,5β)-4,5-dihydro-5-(2-hydroxy-1-methylethyl)-4-methyl-2(3H)-furanone

tert-butylchlorodiphenylsilane

(3S,4S,5R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexanoic acid

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

Downstream raw materials:

C₃₉H₆₀O₅Si₂

C₃₆H₆₀O₄Si₂

C₃₀H₄₀O₃Si

6(R)-<1(S)-Methyl-2-oxobutyl>-4(S)-<1(S),3(RS),5(R),7-tetramethyl-2,4-dioxo-7(E)-decenyl>-2(S),5(S)-dimethyl-2-(p-methoxyphenyl)-1,3-dioxane