(+)-(2R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester

Base Information

• Chemical Name: (+)-(2R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester
• CAS No.: 862877-74-5
• Molecular Formula: C₂₂H₃₂O₅
• Molecular Weight: 376.493
• Mol file: 862877-74-5.mol

Synonyms:(+)-(2R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester

Chemical Property of (+)-(2R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester

There total 7 articles about (+)-(2R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester 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: 93.0%

(+)-(2S,3R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2,3-dihydroxy-2,6-dimethyl-oct-6-enyl ester (862877-73-4) → (+)-(2R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester (862877-74-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.tet.2005.05.050

Reference yield:

(-)-(2'S,1R,4E)-6-benzyloxy-4-methyl-1-(2'-methyloxiranyl)-hex-4-en-1-ol (862877-65-4) → (+)-(2R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester (862877-74-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / Ti(O-iPr)4 / CH₂Cl₂ / 20 °C

2: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With titanium(IV) isopropylate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 2: Swern oxidation;

DOI:10.1016/j.tet.2005.05.050

Reference yield:

(3'E)-3-(5'-benzyloxy-3'-methylpent-3'-enyl)-2,2-dimethyloxirane (55776-46-0) → (+)-(2R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester (862877-74-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / Al(OiPr)3 / toluene / 4 h / Heating

2: 45 percent / (-)-DIPT; t-BuOOH; Ti(O-iPr)4 / CH₂Cl₂ / 6 h / -30 °C

3: 92 percent / Ti(O-iPr)4 / CH₂Cl₂ / 20 °C

4: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; aluminum isopropoxide; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 2: Sharpless epoxidation / 4: Swern oxidation;

DOI:10.1016/j.tet.2005.05.050

upstream raw materials:

(+)-(2S,3R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2,3-dihydroxy-2,6-dimethyl-oct-6-enyl ester

(-)-(2'S,1R,4E)-6-benzyloxy-4-methyl-1-(2'-methyloxiranyl)-hex-4-en-1-ol

(3'E)-3-(5'-benzyloxy-3'-methylpent-3'-enyl)-2,2-dimethyloxirane

3,7-dimethyl-2E,6-octadien-1-yl acetate

Downstream raw materials:

(-)-(2S,6E)-8-benzyloxy-2-hydroxy-2,6-dimethyloct-6-en-3-one

(-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2,6-dimethyl-3-oxo-2-trimethylsilanyloxy-oct-6-enyl ester

(-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester