methyl (1S,3R)-3-tert-butyldiphenylsilyloxymethyl-2,2-dimethylcyclobutane-1-carboxylate

Base Information

• Chemical Name: methyl (1S,3R)-3-tert-butyldiphenylsilyloxymethyl-2,2-dimethylcyclobutane-1-carboxylate
• CAS No.: 528560-23-8
• Molecular Formula: C₂₅H₃₄O₃Si
• Molecular Weight: 410.629
• Mol file: 528560-23-8.mol

Synonyms:methyl (1S,3R)-3-tert-butyldiphenylsilyloxymethyl-2,2-dimethylcyclobutane-1-carboxylate

Chemical Property of methyl (1S,3R)-3-tert-butyldiphenylsilyloxymethyl-2,2-dimethylcyclobutane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,3R)-3-tert-butyldiphenylsilyloxymethyl-2,2-dimethylcyclobutane-1-carboxylate

There total 1 articles about methyl (1S,3R)-3-tert-butyldiphenylsilyloxymethyl-2,2-dimethylcyclobutane-1-carboxylate 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: 90.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-cyclobutanecarboxylic acid (566193-50-8) → methyl (1S,3R)-3-tert-butyldiphenylsilyloxymethyl-2,2-dimethylcyclobutane-1-carboxylate (528560-23-8)

Guidance literature:

In diethyl ether;

DOI:10.1016/S0957-4166(02)00749-8

Reference yield: 75.0%

methyl (1S,3R)-3-tert-butyldiphenylsilyloxymethyl-2,2-dimethylcyclobutane-1-carboxylate (528560-23-8) → (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-cyclobutanecarboxylic acid (566193-50-8)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0957-4166(02)00749-8

Reference yield:

methyl (1S,3R)-3-tert-butyldiphenylsilyloxymethyl-2,2-dimethylcyclobutane-1-carboxylate (528560-23-8) → methyl (1'S,3'S)-2-N-benzyloxycarbonylamino-3-(2',2'-dimethyl-3'-methoxycarbonylcyclobutyl)-(Z)-2-propenoate (528560-25-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / n-Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

2: PDC / CH₂Cl₂ / 6 h / 20 °C

3: t-BuOK / CH₂Cl₂ / 64 h / -78 - 20 °C

With dipyridinium dichromate; potassium tert-butylate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; 3: Wadsworth-Emmons condensation;

DOI:10.1016/S0957-4166(02)00749-8

upstream raw materials:

diazomethane

(1S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-cyclobutanecarboxylic acid

Downstream raw materials:

(1S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-cyclobutanecarboxylic acid

methyl (1'S,3'S)-2-N-benzyloxycarbonylamino-3-(2',2'-dimethyl-3'-methoxycarbonylcyclobutyl)-(Z)-2-propenoate