(1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane

Base Information

• Chemical Name: (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane
• CAS No.: 153861-48-4
• Molecular Formula: C₂₅H₃₄O₃Si
• Molecular Weight: 410.629
• Mol file: 153861-48-4.mol

Synonyms:(1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane

Chemical Property of (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane

There total 9 articles about (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane 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: 97.0%

diiodomethane (75-11-6) + (1Z,4'S)-3-<(tert-Butyldiphenylsilyl)oxy>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-propene (154001-53-3) → (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane (153861-48-4)

Guidance literature:

With diethylzinc; In hexane; dichloromethane; at -23 - 0 ℃;

DOI:10.1039/a904378k

Reference yield:

Chloroiodomethane (593-71-5) + (1Z,4'S)-3-<(tert-Butyldiphenylsilyl)oxy>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-propene (154001-53-3) → (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane (153861-48-4)

Guidance literature:

With diethylzinc; In hexane; 1,2-dichloro-ethane; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00121a047

Reference yield:

(2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol (80532-35-0) → (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane (153861-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Et₃N; DMAP / CH₂Cl₂

2: 97 percent / Et₂Zn / hexane; CH₂Cl₂ / -23 - 0 °C

With dmap; diethylzinc; triethylamine; In hexane; dichloromethane; 1: Etherification / 2: Addition;

DOI:10.1039/a904378k

upstream raw materials:

diiodomethane

(1Z,4'S)-3-<(tert-Butyldiphenylsilyl)oxy>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-propene

Chloroiodomethane

methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

Downstream raw materials:

(S)-1-[(1R,2S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-ethane-1,2-diol

(1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane

(2R,3S)-4-(tert-Butyldiphenylsilyloxy)-2,3-methanobutanoic acid

(4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole