(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one

Base Information

• Chemical Name: (5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one
• CAS No.: 302348-71-6
• Molecular Formula: C₁₉H₂₆O₃Si
• Molecular Weight: 330.499
• Mol file: 302348-71-6.mol

Synonyms:(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one

Chemical Property of (5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one

There total 11 articles about (5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one 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:

benzyltriphenylphosphonium bromide (1449-46-3) + (3S)-3-tert-butyldimethylsilanyloxy-6-oxo-3,6-dihydro-2H-pyran-(2S)-2-carbaldehyde (302348-75-0) → (5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one (302348-71-6) + (5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-trans-styryl-5,6-dihydro-pyran-2-one (302348-89-6)

Guidance literature:

benzyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 0 - 20 ℃;

(3S)-3-tert-butyldimethylsilanyloxy-6-oxo-3,6-dihydro-2H-pyran-(2S)-2-carbaldehyde; In tetrahydrofuran; at -78 ℃; for 0.5h; Further stages.;

DOI:10.1021/ol000179i

Reference yield:

(6S)-6-tert-butyldimethylsilanyloxymethyl-(5S)-5-tert-butyldimethylsilanyloxy-5,6-dihydro-pyran-2-one (302348-85-2) → (5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one (302348-71-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / 5 percent aq. HF / acetonitrile / 6 h / 20 °C

2: 80 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3: n-BuLi; benzyl triphenylphosphonium bromide / tetrahydrofuran / 0.5 h / -78 °C

With n-butyllithium; hydrogen fluoride; benzyltriphenylphosphonium bromide; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; acetonitrile; 2: Dess-Martin oxidation / 3: Wittig reaction;

DOI:10.1016/S0040-4020(01)00355-6

Reference yield:

(6S)-6-tert-butyldimethylsilanyloxymethyl-(5S)-5-hydroxy-5,6-dihydro-pyran-2-one (302348-72-7) → (5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one (302348-71-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / CH₂Cl₂; various solvent(s) / 0.5 h / 0 °C

2: 91 percent / 5 percent aq. HF / acetonitrile / 6 h / 20 °C

3: 80 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4: n-BuLi; benzyl triphenylphosphonium bromide / tetrahydrofuran / 0.5 h / -78 °C

With n-butyllithium; hydrogen fluoride; benzyltriphenylphosphonium bromide; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; acetonitrile; 3: Dess-Martin oxidation / 4: Wittig reaction;

DOI:10.1016/S0040-4020(01)00355-6

upstream raw materials:

triphenyl(phenylmethylene)phosphorane

(3S)-3-tert-butyldimethylsilanyloxy-6-oxo-3,6-dihydro-2H-pyran-(2S)-2-carbaldehyde

(phenyl)methyl 1-phenyl-1H-tetrazol-5-yl sulfone

benzyltriphenylphosphonium bromide

Downstream raw materials:

(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-trans-styryl-5,6-dihydro-pyran-2-one

(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2R,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

(5S)-5-hydroxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one