retinal tert-butyl-dimethylsilylcyanohydrin

Base Information

• Chemical Name: retinal tert-butyl-dimethylsilylcyanohydrin
• CAS No.: 886226-24-0
• Molecular Formula: C₂₇H₄₃NOSi
• Molecular Weight: 425.73
• Mol file: 886226-24-0.mol

Synonyms:retinal tert-butyl-dimethylsilylcyanohydrin

Chemical Property of retinal tert-butyl-dimethylsilylcyanohydrin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of retinal tert-butyl-dimethylsilylcyanohydrin

There total 1 articles about retinal tert-butyl-dimethylsilylcyanohydrin 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: 90.0%

all-trans-Retinal (116-31-4) + tert-butyldimethylsilyl cyanide (56522-24-8) → retinal tert-butyl-dimethylsilylcyanohydrin (886226-24-0)

Guidance literature:

With lithium bromide; In tetrahydrofuran; at 20 ℃; for 20h; Inert atmosphere;

Reference yield: 47.0%

2,6-anhydro-7-deoxy-7-[4-(bromomethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester (886226-23-9) + retinal tert-butyl-dimethylsilylcyanohydrin (886226-24-0) → (2S,3S,4R,5S,6S)-3,4,5-Triacetoxy-6-{4-[(3E,5E,7E,9E)-2-(tert-butyl-dimethyl-silanyloxy)-2-cyano-4,8-dimethyl-10-(2,6,6-trimethyl-cyclohex-1-enyl)-deca-3,5,7,9-tetraenyl]-benzyl}-tetrahydro-pyran-2-carboxylic acid methyl ester (886226-25-1)

Guidance literature:

retinal tert-butyl-dimethylsilylcyanohydrin; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

2,6-anhydro-7-deoxy-7-[4-(bromomethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

DOI:10.1016/j.bmc.2005.12.044

Reference yield:

retinal tert-butyl-dimethylsilylcyanohydrin (886226-24-0) → 2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-L-glycero-L-gulo-heptonic acid

Guidance literature:

Multi-step reaction with 3 steps

1.1: hexamethyldisilazane lithium salt / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 47 percent / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran; H₂O / 1 h

3.1: K₂CO₃ / methanol / 20 h / 4 °C

3.2: 82 percent / KOH / methanol / 20 h / 4 °C

With tetrabutyl ammonium fluoride; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; water;

DOI:10.1016/j.bmc.2005.12.044

upstream raw materials:

all-trans-Retinal

tert-butyldimethylsilyl cyanide

Downstream raw materials:

(2S,3S,4R,5S,6S)-3,4,5-Triacetoxy-6-{4-[(3E,5E,7E,9E)-2-(tert-butyl-dimethyl-silanyloxy)-2-cyano-4,8-dimethyl-10-(2,6,6-trimethyl-cyclohex-1-enyl)-deca-3,5,7,9-tetraenyl]-benzyl}-tetrahydro-pyran-2-carboxylic acid methyl ester

2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester