methyl (2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate

Base Information

• Chemical Name: methyl (2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate
• CAS No.: 949148-90-7
• Molecular Formula: C₂₀H₂₈O₃Si
• Molecular Weight: 344.526
• Mol file: 949148-90-7.mol

Synonyms:methyl (2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate

Chemical Property of methyl (2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate

There total 2 articles about methyl (2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate 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: 65.0%

(E)-3-(benzyldimethylsilyl)-2-methylacrylaldehyde (949148-82-7) + methyl(2S,3S)-E-3-(dimethylphenylsilyl)-2-(trimethylsiloxy)-hex-4-enoate → methyl (2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate (949148-90-7) + C11H16O3

Guidance literature:

With 2,6-di-tert-butyl-pyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -78 - -20 ℃;

DOI:10.1021/ol701427k

Reference yield:

(E)-3-(benzyldimethylsilyl)-2-methylprop-2-en-1-ol → methyl (2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate (949148-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / MnO₂ / CH₂Cl₂ / 0.17 h / 20 °C

2: 65 percent / 2,6-di-tert-butylpyridine; trimethylsilyl trifluoromethanesulfonate / acetonitrile; CH₂Cl₂ / -78 - -20 °C

With manganese(IV) oxide; 2,6-di-tert-butyl-pyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile;

DOI:10.1021/ol701427k

Reference yield:

methyl (2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate (949148-90-7) → C19H28O2Si

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.666667h;

DOI:10.1021/ol701427k

upstream raw materials:

(E)-3-(benzyldimethylsilyl)-2-methylacrylaldehyde

Downstream raw materials:

((2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)methanol

2-((2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

methyl 2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetate