(1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol

Base Information

• Chemical Name: (1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol
• CAS No.: 131472-78-1
• Molecular Formula: C₂₈H₃₅NO₂Si
• Molecular Weight: 445.677
• Mol file: 131472-78-1.mol

Synonyms:(1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol

Chemical Property of (1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol

There total 7 articles about (1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol 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:

Benzophenone imine (1013-88-3) → (1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol (131472-78-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / CH₂Cl₂

2: 92 percent / imidazole / dimethylformamide / 24 h

3: 1) DIBAL-TRIBAL / 1) CH₂Cl₂, hexane, -78 deg C, 15 min, 2) Et₂O, a) -78 deg C, 1 h, b) r.t., 1 h

With 1H-imidazole; triisobutylaluminum; diisobutylaluminium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00046a032

Reference yield:

dibenzo-imino-methyl-L-serinate (133157-01-4,218766-08-6) → (1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol (131472-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / imidazole / dimethylformamide / 24 h

2: 1) DIBAL-TRIBAL / 1) CH₂Cl₂, hexane, -78 deg C, 15 min, 2) Et₂O, a) -78 deg C, 1 h, b) r.t., 1 h

With 1H-imidazole; triisobutylaluminum; diisobutylaluminium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00046a032

Reference yield:

methyl O-tert-butyldimethylsilyl-N-(diphenylmethylene)-L-serinate (131472-75-8) + phenylmagnesium bromide → (1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol (131472-78-1)

Guidance literature:

With triisobutylaluminum; diisobutylaluminium hydride; Yield given. Multistep reaction; 1) CH₂Cl₂, hexane, -78 deg C, 15 min, 2) Et₂O, a) -78 deg C, 1 h, b) r.t., 1 h;

DOI:10.1021/jo00046a032

upstream raw materials:

methyl O-tert-butyldimethylsilyl-N-(diphenylmethylene)-L-serinate

phenylmagnesium bromide

Benzophenone imine

dibenzo-imino-methyl-L-serinate

Downstream raw materials:

Toluene-4-sulfonic acid (4S,5S)-2-oxo-5-phenyl-oxazolidin-4-ylmethyl ester

L-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol

(4S,5S)-4-Morpholin-4-ylmethyl-5-phenyl-oxazolidin-2-one

(1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanol