methyl (2R,3S,6R,7S)-2,6-dihydroxy-3,7,11-trimethyldodecanoate

Base Information

• Chemical Name: methyl (2R,3S,6R,7S)-2,6-dihydroxy-3,7,11-trimethyldodecanoate
• CAS No.: 102616-17-1
• Molecular Formula: C₁₆H₃₂O₄
• Molecular Weight: 288.428
• Mol file: 102616-17-1.mol

Synonyms:

Chemical Property of methyl (2R,3S,6R,7S)-2,6-dihydroxy-3,7,11-trimethyldodecanoate

Chemical Property:

• Vapor Pressure: 2.91E-08mmHg at 25°C
• Boiling Point: 405.4°C at 760 mmHg
• Flash Point: 135.9°C
• Density: 0.984g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl (2R,3S,6R,7S)-2,6-dihydroxy-3,7,11-trimethyldodecanoate

There total 11 articles about methyl (2R,3S,6R,7S)-2,6-dihydroxy-3,7,11-trimethyldodecanoate 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: 81.0%

methyl (4E,8E)-(2S*,3R*,6R*,7R*)-2,6-bis(phenylmethoxy)-3,7,11-trimethyldodeca-4,8-dienoate (102616-15-9) → methyl (2R*,3S*,6R*,7S*)-2,6-dihydroxy-3,7,11-trimethyldodecanoate (102616-17-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 48h;

DOI:10.1021/jo00226a032

Reference yield:

(E)-(2R*,3R*)-3,7-dimethyl-2-(phenylmethoxy)oct-4-enal (102616-12-6) → methyl (2R*,3S*,6R*,7S*)-2,6-dihydroxy-3,7,11-trimethyldodecanoate (102616-17-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / MgBr₂ / diethyl ether / -78 °C

2: pyridine

4: H₂ / Pd/C / methanol

With pyridine; hydrogen; magnesium bromide; palladium on activated charcoal; In methanol; diethyl ether;

DOI:10.1021/jo00364a058

Reference yield:

(E)-(2R*,3R*)-3,7-dimethyl-2-(phenylmethoxy)oct-4-enol (102616-11-5) → methyl (2R*,3S*,6R*,7S*)-2,6-dihydroxy-3,7,11-trimethyldodecanoate (102616-17-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / (COCl)2, DMSO

2: 85 percent / MgBr₂ / diethyl ether / -78 °C

3: pyridine

5: H₂ / Pd/C / methanol

With pyridine; oxalyl dichloride; hydrogen; dimethyl sulfoxide; magnesium bromide; palladium on activated charcoal; In methanol; diethyl ether;

DOI:10.1021/jo00364a058

upstream raw materials:

methyl (4E,8E)-(2S*,3R*,6R*,7R*)-2,6-bis(phenylmethoxy)-3,7,11-trimethyldodeca-4,8-dienoate

(Z)-6-methyl-2-hepten-4-ol

(Z)-2-methylhept-5-en-4-ol (phenylmethoxy)acetate

(E)-(2R*,3R*)-3,7-dimethyl-2-(phenylmethoxy)oct-4-enal

Downstream raw materials:

(3R*,7R*)-3,7,11-trimethyldodecan-1-ol

Refernces

• 1、 Kallmerten, James,Balestra, Michael. "An Effective Strategy for Acyclic Synthesis via Interative Rearrangement of Allylic Glycolates. Synthesis of a Pine Sawfly Pheromone". . p. 2855 - 2857. Retrieved 2007/10/02.