(+/-)-(6-endo,7-exo)-7-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3-methoxy-6-methyl-5-(2-propenyl)bicyclo<3.2.1>oct-3-ene-2,8-dione

Base Information

• Chemical Name: (+/-)-(6-endo,7-exo)-7-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3-methoxy-6-methyl-5-(2-propenyl)bicyclo<3.2.1>oct-3-ene-2,8-dione
• CAS No.: 127086-34-4
• Molecular Formula: C₂₆H₃₆O₅Si
• Molecular Weight: 456.654
• Mol file: 127086-34-4.mol

Synonyms:(+/-)-(6-endo,7-exo)-7-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3-methoxy-6-methyl-5-(2-propenyl)bicyclo<3.2.1>oct-3-ene-2,8-dione

Chemical Property of (+/-)-(6-endo,7-exo)-7-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3-methoxy-6-methyl-5-(2-propenyl)bicyclo<3.2.1>oct-3-ene-2,8-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(6-endo,7-exo)-7-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3-methoxy-6-methyl-5-(2-propenyl)bicyclo<3.2.1>oct-3-ene-2,8-dione

There total 1 articles about (+/-)-(6-endo,7-exo)-7-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3-methoxy-6-methyl-5-(2-propenyl)bicyclo<3.2.1>oct-3-ene-2,8-dione 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:

(+/-)-(6-endo,7-exo)-7-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3-methoxy-6-methyl-5-<3-<(methylsulfonyl)oxy>propyl>bicyclo<3.2.1>oct-3-ene-2,8-dione → (+/-)-(6-endo,7-exo)-7-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3-methoxy-6-methyl-5-(2-propenyl)bicyclo<3.2.1>oct-3-ene-2,8-dione (127086-34-4)

Guidance literature:

With sodium tetrahydroborate; sodium periodate; diphenyl diselenide; Yield given. Multistep reaction; 1.) ethanol;

DOI:10.1021/jo00072a017

Reference yield: 98.0%

(+/-)-(6-endo,7-exo)-7-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3-methoxy-6-methyl-5-(2-propenyl)bicyclo<3.2.1>oct-3-ene-2,8-dione (127086-34-4) → (+/-)-(2α,4α,5β,5aα)-4-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-2,5a-mathano-7-methoxy-5-methyl-8H-2,3,4,5-tetrahydro-1-benzoxepin-8-one (127102-42-5)

Guidance literature:

With titanium tetrachloride; In dichloromethane-d2; at -78 - 25 ℃; for 1h;

DOI:10.1021/ja00165a087

Reference yield:

(+/-)-(6-endo,7-exo)-7-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3-methoxy-6-methyl-5-(2-propenyl)bicyclo<3.2.1>oct-3-ene-2,8-dione (127086-34-4) → (+/-)-(2α,4α,5β,5aα)-4-(4-hydroxy-3-methoxyphenyl)-2,5a-methano-7-methoxy-5-methyl-8H-2,3,4,5-tetrahydro-1-benzoxepin-8-one

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / TiCl₄ / CD₂Cl₂ / 1,) -78 deg C, 5 min, 2.) room temp., 5 min

2: 93 percent / (n-Bu)4NF / CDCl₃ / 0.17 h / Ambient temperature

With tetrabutyl ammonium fluoride; titanium tetrachloride; In chloroform-d1; dichloromethane-d2;

DOI:10.1021/jo00072a017

Downstream raw materials:

(+/-)-(2α,4α,5β,5aα)-4-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-2,5a-mathano-7-methoxy-5-methyl-8H-2,3,4,5-tetrahydro-1-benzoxepin-8-one