(1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-en-1-ol

Base Information

• Chemical Name: (1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-en-1-ol
• CAS No.: 155128-11-3
• Molecular Formula: C₁₆H₂₄O₃
• Molecular Weight: 264.365
• Mol file: 155128-11-3.mol

Synonyms:(1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-en-1-ol

Chemical Property of (1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-en-1-ol

There total 11 articles about (1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-en-1-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: 69.0%

C15H30O2S2Si (155128-04-4) + benzaldehyde (100-52-7) + (methoxymethoxy)methyl chloride (122776-88-9) + chloromethyl methyl ether (107-30-2) → (1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxymethoxy)-1-phenylhex-3-en-1-ol + (1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-en-1-ol (155128-11-3)

Guidance literature:

C₁₅H₃₀O₂S₂Si; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 3h; Inert atmosphere; Reflux;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 19h;

benzaldehyde; (methoxymethoxy)methyl chloride; chloromethyl methyl ether; optical yield given as %de; diastereoselective reaction; Further stages;

DOI:10.1039/c0ob01084g

Reference yield: 38.0%

chloromethyl methyl ether (107-30-2) + (1S,5R,3Z)-3,5-dimethyl-1-phenylhex-3-ene-1,6-diol → (2R,6S,3Z)-2,4-dimethyl-6-(methoxymethoxy)-6-phenylhex-3-en-1-ol (1309803-72-2) + (1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-en-1-ol (155128-11-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 14.5h;

DOI:10.1039/c0ob01084g

Reference yield:

C14H28O2S2Si → (1S,5R,3Z)-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-en-1-ol (155128-11-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: mineral oil; benzene / 15 h / 20 °C

2.1: toluene / 15 h / Reflux

3.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 3 h / Inert atmosphere; Reflux

3.2: 19 h / 0 - 20 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; mineral oil; benzene;

DOI:10.1039/c0ob01084g

upstream raw materials:

benzaldehyde

chloromethyl methyl ether

(2E,4R)-5-((tert-butyldimethylsilyl)oxy)-2,4-dimethylpent-2-en-1-ol

(2E,4R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-2,4-dimethylpent-2-enoate

Downstream raw materials:

(1S,5R,3Z)-1-[(S)-2-acetoxy-2-phenylacetoxy]-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-ene

(1S,5R,3Z)-1-[(R)-2-acetoxy-2-phenylacetoxy]-3,5-dimethyl-6-(methoxymethoxy)-1-phenylhex-3-ene

4-Nitro-benzoic acid (Z)-(1R,5R)-6-methoxymethoxy-3,5-dimethyl-1-phenyl-hex-3-enyl ester