methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxy methyl-2'-trimethylsilyloxy-2'-methyl-bicyclo[3.1.1]hept-6'-yl)-4-tert-butyldiphenylsilyloxy-2-methyl-2-pentenoate

Base Information

Chemical Name:methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxy methyl-2'-trimethylsilyloxy-2'-methyl-bicyclo[3.1.1]hept-6'-yl)-4-tert-butyldiphenylsilyloxy-2-methyl-2-pentenoate
CAS No.:909280-41-7
Molecular Formula:C₃₇H₅₄O₆Si₂
Molecular Weight:651.003
Hs Code.:

methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxy methyl-2'-trimethylsilyloxy-2'-methyl-bicyclo[3.1.1]hept-6'-yl)-4-tert-butyldiphenylsilyloxy-2-methyl-2-pentenoate

Synonyms:methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxy methyl-2'-trimethylsilyloxy-2'-methyl-bicyclo[3.1.1]hept-6'-yl)-4-tert-butyldiphenylsilyloxy-2-methyl-2-pentenoate

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Chemical Property of methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxy methyl-2'-trimethylsilyloxy-2'-methyl-bicyclo[3.1.1]hept-6'-yl)-4-tert-butyldiphenylsilyloxy-2-methyl-2-pentenoate

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Technology Process of methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxy methyl-2'-trimethylsilyloxy-2'-methyl-bicyclo[3.1.1]hept-6'-yl)-4-tert-butyldiphenylsilyloxy-2-methyl-2-pentenoate

There total 6 articles about methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxy methyl-2'-trimethylsilyloxy-2'-methyl-bicyclo[3.1.1]hept-6'-yl)-4-tert-butyldiphenylsilyloxy-2-methyl-2-pentenoate 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: 59.0%

: 909280-39-3
methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxymethyl-2'-trimethylsilyloxy-3'-methyl-bicyclo[3.1.1]-hept-6'-yl)-4-hydroxy-2-methyl-2-pentenoate

: 58479-61-1
tert-butylchlorodiphenylsilane

: 909280-41-7
methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxy methyl-2'-trimethylsilyloxy-2'-methyl-bicyclo[3.1.1]hept-6'-yl)-4-tert-butyldiphenylsilyloxy-2-methyl-2-pentenoate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1016/j.tet.2006.06.011

Reference yield:

: 909280-24-6
(1R,2R,5S,6S)-2-hydroxy-2-methyl-6-(2-propenyl)bicyclo[3.1.1]hept-6-yl-methanol

: 909280-41-7
methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxy methyl-2'-trimethylsilyloxy-2'-methyl-bicyclo[3.1.1]hept-6'-yl)-4-tert-butyldiphenylsilyloxy-2-methyl-2-pentenoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / pyridine / CH₂Cl₂ / 12 h

2.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

3.1: ozone / CH₂Cl₂ / -78 °C

3.2: 95 percent / dimethyl sulfide / CH₂Cl₂ / -78 - 20 °C

4.1: 46 percent / anhydrous CrCl₂; NiCl₂ / dimethylformamide / 20 °C

5.1: 59 percent / Et₃N; DMAP / CH₂Cl₂ / 48 h / 20 °C

With pyridine; chromium dichloride; dmap; ozone; triethylamine; nickel dichloride; In dichloromethane; N,N-dimethyl-formamide; 4.1: Nozaki-Hiyama-Kishi reaction;
DOI:10.1016/j.tet.2006.06.011

Reference yield:

: 909280-27-9
(1R,2R,5S,6S)-2-hydroxy-2-methyl-6-(2-propenyl)-bicyclo[3.1.1]hept-6-yl-methyl acetate

: 909280-41-7
methyl (1'R,2'R,4S,5'S,6'S)-(E)-5-(6'-acetoxy methyl-2'-trimethylsilyloxy-2'-methyl-bicyclo[3.1.1]hept-6'-yl)-4-tert-butyldiphenylsilyloxy-2-methyl-2-pentenoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

2.1: ozone / CH₂Cl₂ / -78 °C

2.2: 95 percent / dimethyl sulfide / CH₂Cl₂ / -78 - 20 °C

3.1: 46 percent / anhydrous CrCl₂; NiCl₂ / dimethylformamide / 20 °C

4.1: 59 percent / Et₃N; DMAP / CH₂Cl₂ / 48 h / 20 °C

With chromium dichloride; dmap; ozone; triethylamine; nickel dichloride; In dichloromethane; N,N-dimethyl-formamide; 3.1: Nozaki-Hiyama-Kishi reaction;
DOI:10.1016/j.tet.2006.06.011