(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-(R)-oxiranyl-propan-2-ol

Base Information

• Chemical Name: (S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-(R)-oxiranyl-propan-2-ol
• CAS No.: 410077-39-3
• Molecular Formula: C₂₂H₃₀O₃Si
• Molecular Weight: 370.564
• Mol file: 410077-39-3.mol

Synonyms:(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-(R)-oxiranyl-propan-2-ol

Chemical Property of (S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-(R)-oxiranyl-propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-(R)-oxiranyl-propan-2-ol

There total 4 articles about (S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-(R)-oxiranyl-propan-2-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: 91.0%

(4S,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-iodomethyl-4-methyl-[1,3]dioxan-2-one (410077-37-1) → (S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-(R)-oxiranyl-propan-2-ol (410077-39-3)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2.5h;

DOI:10.1021/ol017273z

Reference yield:

(S)-1-(tert-butyldiphenylsilyloxy)methyl-1-methyloxirane (184091-30-3) → (S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-(R)-oxiranyl-propan-2-ol (410077-39-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: CuI / tetrahydrofuran / 1 h / -40 °C

1.2: 83 percent / tetrahydrofuran / -45 - 0 °C

2.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

2.2: 99 percent / tetrahydrofuran / 1 h / 20 °C

3.1: IBr / diethyl ether; CH₂Cl₂ / 3.5 h / -100 - -78 °C

4.1: 91 percent / K₂CO₃ / methanol / 2.5 h / 20 °C

With copper(l) iodide; sodium hexamethyldisilazane; iodine(I) bromide; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/ol017273z

Reference yield:

1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol (410077-69-9) → (S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-(R)-oxiranyl-propan-2-ol (410077-39-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

1.2: 99 percent / tetrahydrofuran / 1 h / 20 °C

2.1: IBr / diethyl ether; CH₂Cl₂ / 3.5 h / -100 - -78 °C

3.1: 91 percent / K₂CO₃ / methanol / 2.5 h / 20 °C

With sodium hexamethyldisilazane; iodine(I) bromide; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/ol017273z

upstream raw materials:

(4S,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-iodomethyl-4-methyl-[1,3]dioxan-2-one

(S)-1-(tert-butyldiphenylsilyloxy)methyl-1-methyloxirane

1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol

carbonic acid tert-butyl ester 1-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-but-3-enyl ester

Downstream raw materials:

C₃₇H₅₂O₅S₂Si

C₆₅H₁₁₂O₁₅Si₃

C₄₃H₇₄O₉Si₂

{(2R,4S,6S,8S,10S)-4-Acetoxy-8-[(R)-4-(4-methoxy-benzyloxy)-3-methyl-2-methylene-butyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl}-acetic acid