(2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl ester

Base Information

• Chemical Name: (2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl ester
• CAS No.: 1027201-42-8
• Molecular Formula: C₂₀H₃₄O₃Si₂
• Molecular Weight: 378.659
• Mol file: 1027201-42-8.mol

Synonyms:(2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl ester

Chemical Property of (2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl ester

There total 1 articles about (2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl 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: 83.0%

isopropyl alcohol (67-63-0,8013-70-5) + methyl (2R,3S)-(E)-3-(dimethyl(phenyl)silyl)-2-(trimethylsilyloxy)-hex-4-enoate → (2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl ester (1027201-42-8)

Guidance literature:

With Otera's catalyst; for 120h; Heating;

DOI:10.1021/jo0610412

Reference yield: 73.0%

[4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile (850404-87-4) + (2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl ester (1027201-42-8) → (2S,5S,6R)-6-{(2S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-cyanomethyltetrahydro-2H-pyran-2-yl]-2-methoxypropyl}-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid isopropyl ester (850404-96-5) + (2S,5S,6S)-6-{(2S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-cyanomethyltetrahydro-2H-pyran-2-yl]-2-methoxypropyl}-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid isopropyl ester

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -50 ℃; for 12h;

DOI:10.1021/jo0610412

Reference yield:

(2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl ester (1027201-42-8) → {(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-((2S,3E)-2-hydroxy-6-methylhept-3-enyl)-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

Guidance literature:

Multi-step reaction with 6 steps

1: 73 percent / trimethylsilyl triflate / CH₂Cl₂ / 12 h / -50 °C

2: 89 percent / hydrogen / Pd/C / ethyl acetate / 18 h

3: 93 percent / DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

4: LiHMDS / tetrahydrofuran / 4.5 h / -78 °C

5: 82 mg / mercury acetate / tetrahydrofuran; H₂O / 0.25 h

6: bis(cyclopentadienyl)zirconium chloride hydride; ZnMe₂ / CH₂Cl₂; toluene / 3.5 h / 0 °C

With Schwartz's reagent; trimethylsilyl trifluoromethanesulfonate; mercury(II) diacetate; hydrogen; dimethyl zinc(II); diisobutylaluminium hydride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene; 4: wITTIG REACTION;

DOI:10.1021/jo0610412

upstream raw materials:

isopropyl alcohol

Downstream raw materials:

(2S,5S,6R)-6-{(2S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-cyanomethyltetrahydro-2H-pyran-2-yl]-2-methoxypropyl}-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid isopropyl ester

{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-2-methoxy-3-((2R,3S,6S)-3-methyl-6-(oxoethyl)tetrahydro-2H-pyran-2-yl)propyl]tetrahydro-2H-pyran-2-yl}acetonitrile

(2S,5S,6R)-6-{(2S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-cyanomethyltetrahydro-2H-pyran-2-yl]-2-methoxypropyl}-5-methyltetrahydro-2H-pyran-2-carboxylic acid isopropyl ester