(2S,3R,5R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-4-hepten-7-ol

Base Information

• Chemical Name: (2S,3R,5R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-4-hepten-7-ol
• CAS No.: 124755-28-8
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 124755-28-8.mol

Synonyms:(2S,3R,5R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-4-hepten-7-ol

Chemical Property of (2S,3R,5R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-4-hepten-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-4-hepten-7-ol

There total 1 articles about (2S,3R,5R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-4-hepten-7-ol 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:

(E)-(2R,5R,6S)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-3-heptene-1,5-diol (124755-27-7) + benzaldehyde (100-52-7) → (2S,3R,5R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-4-hepten-7-ol (124755-28-8)

Guidance literature:

With pyridinium p-toluenesulfonate; Yield given. Multistep reaction; 1) EtOH, r.t., 3 h 2) CH₂Cl₂;

DOI:10.1021/jo00292a031

Reference yield: 92.0%

(2S,3R,5R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-4-hepten-7-ol (124755-28-8) → (2S,3S,4S,6R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-heptan-7-ol (124755-29-9)

Guidance literature:

With [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate; hydrogen; In dichloromethane; for 0.166667h; under 33614.6 Torr;

DOI:10.1021/jo00292a031

Reference yield:

(2S,3R,5R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-4-hepten-7-ol (124755-28-8) → (2S,3S,4S,6R)-3-(benzyloxy)-7-<(p-methoxybenzyl)oxy>-2,4,6-trimethyl-1-heptanol (124755-32-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / BF₄, H₂ / CH₂Cl₂ / 0.17 h / 33614.6 Torr

2: 1) NaH / 1) DMF, r.t., 3 h

3: 93 percent / (i-Bu)2AlH / CH₂Cl₂ / 6 h / 0 °C

With [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate; hydrogen; sodium hydride; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1021/jo00292a031

upstream raw materials:

(E)-(2R,5R,6S)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-3-heptene-1,5-diol

benzaldehyde

Downstream raw materials:

(2S,3S,4S,6R)-1,3-(benzylidenedioxy)-2,4,5-trimethyl-heptan-7-ol

(2S,3S,4S,6R)-3-(benzyloxy)-7-<(p-methoxybenzyl)oxy>-2,4,6-trimethyl-1-heptanol

(2S,3S,4S,6R)-1,3-(benzylidenedioxy)-7-<(p-methoxybenzyl)oxy>-2,4,6-trimethylheptane