1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene

Base Information

• Chemical Name: 1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene
• CAS No.: 103905-01-7
• Molecular Formula: C₂₈H₄₀O₅S
• Molecular Weight: 488.689
• Mol file: 103905-01-7.mol

Synonyms:1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene

Chemical Property of 1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene

There total 3 articles about 1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene 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%

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate (37905-02-5) + {[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]sulfonyl}benzene (56691-74-8) → 1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene (103905-01-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 5h;

DOI:10.1246/cl.1985.1883

Reference yield:

3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3,8022-83-1) → 1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene (103905-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1: SeO₂, salicylic acid, tert-butyl hydroperoxide / CH₂Cl₂ / 27 h / Ambient temperature

2: PDC / CH₂Cl₂ / 10 h / Ambient temperature

3: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h

With tert.-butylhydroperoxide; dipyridinium dichromate; n-butyllithium; selenium(IV) oxide; salicylic acid; In dichloromethane;

DOI:10.1021/jo00370a017

Reference yield:

8-hydroxygeranyl acetate (37905-03-6) → 1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene (103905-01-7)

Guidance literature:

Multi-step reaction with 2 steps

1: PDC / CH₂Cl₂ / 10 h / Ambient temperature

2: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h

With dipyridinium dichromate; n-butyllithium; In dichloromethane;

DOI:10.1021/jo00370a017

upstream raw materials:

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

{[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]sulfonyl}benzene

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

8-hydroxygeranyl acetate

Downstream raw materials:

1-acetoxy-3,7-dimethyl-8-methoxymethoxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene

(2E,6E)-9-Benzenesulfonyl-3,7-dimethyl-8-(tetrahydro-pyran-2-yloxy)-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dien-1-ol

1-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene

(7E,9E,11E,13Z)-retinyl acetate

Refernces

• 1、 Otera,Misawa,Onishi,et al.. "Stereocontrolled synthesis of vitamin A through a double elimination reaction. A novel convergent C10 + C10 route". . p. 3834 - 3838. Retrieved 2007/10/02.