1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-[(1E)-3-oxo-1-propenyl ]-3,4-bis(phenylmethoxy)-, phenylmethyl ester, (2R,3R,4R,5S)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-[(1E)-3-oxo-1-propenyl ]-3,4-bis(phenylmethoxy)-, phenylmethyl ester, (2R,3R,4R,5S)-
• CAS No.: 394706-23-1
• Molecular Formula: C46H49NO6Si
• Molecular Weight: 739.984
• Mol file: 394706-23-1.mol

Synonyms:

Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-[(1E)-3-oxo-1-propenyl ]-3,4-bis(phenylmethoxy)-, phenylmethyl ester, (2R,3R,4R,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-[(1E)-3-oxo-1-propenyl ]-3,4-bis(phenylmethoxy)-, phenylmethyl ester, (2R,3R,4R,5S)-

There total 2 articles about 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-[(1E)-3-oxo-1-propenyl ]-3,4-bis(phenylmethoxy)-, phenylmethyl ester, (2R,3R,4R,5S)- 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: 44.0%

(triphenylphosphoranylidene)acetaldehyde (2136-75-6) + [(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]carbaldehyde (394706-11-7) → (E)-3-[(2'S,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]propenal (394706-23-1)

Guidance literature:

In dichloromethane; at 20 ℃; for 36h;

DOI:10.1016/S0957-4166(01)00440-2

Reference yield:

(2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (340970-04-9) → (E)-3-[(2'S,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]propenal (394706-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / 4 Angstroem MS; N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 4 h / 20 °C

2: 44 percent / CH₂Cl₂ / 36 h / 20 °C

With tetrapropylammonium perruthennate; 4 Angstroem MS; 4-methylmorpholine N-oxide; In dichloromethane;

DOI:10.1016/S0957-4166(01)00440-2

Reference yield: 45.0%

(E)-3-[(2'S,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]propenal (394706-23-1) → (1R,2R,3R,7aS)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethylpyrrolizidine (291510-06-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 7h; under 3040 Torr;

DOI:10.1016/S0957-4166(01)00440-2

upstream raw materials:

(triphenylphosphoranylidene)acetaldehyde

[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]carbaldehyde

(2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

Downstream raw materials:

(1R,2R,3R,7aS)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethylpyrrolizidine

(1R,2R,3R,7aS)-1,2-dibenzyloxy-3-hydroxymethylpyrrolizidine