Bicyclo[2.2.1]heptan-2-one, 1-[[[(2S,5R)-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-[3-(phenyl methoxy)propyl]-1-pyrrolidinyl]sulfonyl]methyl]-7,7-dimethyl-, (1S,4R)-

Base Information

• Chemical Name: Bicyclo[2.2.1]heptan-2-one, 1-[[[(2S,5R)-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-[3-(phenyl methoxy)propyl]-1-pyrrolidinyl]sulfonyl]methyl]-7,7-dimethyl-, (1S,4R)-
• CAS No.: 916152-74-4
• Molecular Formula: C41H55NO5SSi
• Molecular Weight: 702.043
• Mol file: 916152-74-4.mol

Synonyms:

Chemical Property of Bicyclo[2.2.1]heptan-2-one, 1-[[[(2S,5R)-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-[3-(phenyl methoxy)propyl]-1-pyrrolidinyl]sulfonyl]methyl]-7,7-dimethyl-, (1S,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[2.2.1]heptan-2-one, 1-[[[(2S,5R)-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-[3-(phenyl methoxy)propyl]-1-pyrrolidinyl]sulfonyl]methyl]-7,7-dimethyl-, (1S,4R)-

There total 2 articles about Bicyclo[2.2.1]heptan-2-one, 1-[[[(2S,5R)-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-[3-(phenyl methoxy)propyl]-1-pyrrolidinyl]sulfonyl]methyl]-7,7-dimethyl-, (1S,4R)- 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: 93.0%

(2R,5S)-2-(3-Benzyloxy-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidine (916152-63-1) + Camphorsulfonyl chloride (21286-54-4) → (1S,4R)-1-[(2R,5S)-2-(3-Benzyloxy-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidine-1-sulfonylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one (916152-74-4)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2006.05.088

Reference yield:

(S)-5-(3-(benzyloxy)propyl)-2-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydro-2H-pyrrole (716336-76-4) → (1S,4R)-1-[(2R,5S)-2-(3-Benzyloxy-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidine-1-sulfonylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one (916152-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / hydrogen / PtO₂ / ethanol / 1 h / 20 °C / 760 Torr

2: 93 percent / Et₃N; DMAP / acetonitrile / 24 h / 20 °C

With dmap; hydrogen; triethylamine; platinum(IV) oxide; In ethanol; acetonitrile;

DOI:10.1016/j.tet.2006.05.088

Reference yield: 95.0%

(1S,4R)-1-[(2R,5S)-2-(3-Benzyloxy-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidine-1-sulfonylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one (916152-74-4) → (2S,5R)-5-(3-benzyloxypropyl)-2-(hydroxymethyl)-1-((1S)-10-camphorsulfonyl)-pyrrolidine

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/j.tet.2006.05.088

upstream raw materials:

(2R,5S)-2-(3-Benzyloxy-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidine

Camphorsulfonyl chloride

(S)-5-(3-(benzyloxy)propyl)-2-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydro-2H-pyrrole