2-Pyrrolidinemethanol, 1-[(4-methylphenyl)sulfonyl]-3,4-bis(phenylmethoxy)-5-[(phenylmethoxy) methyl]-, (2S,3R,4R,5S)-

Base Information

• Chemical Name: 2-Pyrrolidinemethanol, 1-[(4-methylphenyl)sulfonyl]-3,4-bis(phenylmethoxy)-5-[(phenylmethoxy) methyl]-, (2S,3R,4R,5S)-
• CAS No.: 881185-65-5
• Molecular Formula: C34H37NO6S
• Molecular Weight: 587.737
• Mol file: 881185-65-5.mol

Synonyms:

Chemical Property of 2-Pyrrolidinemethanol, 1-[(4-methylphenyl)sulfonyl]-3,4-bis(phenylmethoxy)-5-[(phenylmethoxy) methyl]-, (2S,3R,4R,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Pyrrolidinemethanol, 1-[(4-methylphenyl)sulfonyl]-3,4-bis(phenylmethoxy)-5-[(phenylmethoxy) methyl]-, (2S,3R,4R,5S)-

There total 6 articles about 2-Pyrrolidinemethanol, 1-[(4-methylphenyl)sulfonyl]-3,4-bis(phenylmethoxy)-5-[(phenylmethoxy) methyl]-, (2S,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: 99.0%

(2S,3R,4R,5S)-2-acetoxymethyl-3,4-di-O-benzyl-5-benzyloxymethyl-N-(p-toluenesulfonamido)pyrrolidine (881185-59-7) → (2S,3R,4R,5S)-3,4-bis-(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)-N-(p-toluenesulfonamido)pyrrolidine (881185-65-5)

Guidance literature:

With sodium carbonate; In methanol; for 1.5h; Reflux;

DOI:10.1021/jo3004452

Reference yield: 84.0%

(2S,3R,4R,5S)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-2-(tert-butyldimethylsilanyloxymethyl)-1-N-(p-tolylsulfonyl)pyrrolidine → (2S,3R,4R,5S)-3,4-bis-(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)-N-(p-toluenesulfonamido)pyrrolidine (881185-65-5)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1002/ejoc.201402943

Reference yield:

3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol (881185-41-7) → (2S,3R,4R,5S)-3,4-bis-(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)-N-(p-toluenesulfonamido)pyrrolidine (881185-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / pyridine; DMAP / 1 h / -15 °C

2: 88 percent / PPh₃; DEAD / tetrahydrofuran / 0.25 h / 0 °C

3: 93 percent / Na₂CO₃ / methanol / 12 h / 20 °C

With pyridine; dmap; sodium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 2: Mitsunobu cyclization;

DOI:10.1016/j.tet.2005.11.037

upstream raw materials:

(2S,3R,4R,5S)-2-acetoxymethyl-3,4-di-O-benzyl-5-benzyloxymethyl-N-(p-toluenesulfonamido)pyrrolidine

3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

Acetic acid (2S,3R,4S)-3,4-bis-benzyloxy-5-benzyloxymethyl-5-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

Downstream raw materials:

(2S,3R,4R,5S)-2-(9-adeninylmethyl)-3,4-dihydroxy-5-(hydroxymethyl)-N-(p-toluenesulfonamido)pyrrolidine

(4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-ol

(4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-yl trifluoromethanesulfonate

(2S,3S,4R,5S)-2-(9-adenylmethyl)-(3-O,5-C-methylene)-N-(ptoluenesulfonamido)pyrrolidine