(2S,3S,4R)-1-benzyl-2-[(1R)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol

Base Information

• Chemical Name: (2S,3S,4R)-1-benzyl-2-[(1R)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol
• CAS No.: 117781-07-4
• Molecular Formula: C₁₃H₁₉NO₄
• Molecular Weight: 253.298
• Mol file: 117781-07-4.mol

Synonyms:3,4-Pyrrolidinediol,2-(1,2-dihydroxyethyl)-1-(phenylmethyl)-, [2S-[2a(R*),3b,4b]]- (9CI)

Chemical Property of (2S,3S,4R)-1-benzyl-2-[(1R)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol

Chemical Property:

• Vapor Pressure: 2.07E-10mmHg at 25°C
• Boiling Point: 489.8°Cat760mmHg
• Flash Point: 289.9°C
• Density: 1.386g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3S,4R)-1-benzyl-2-[(1R)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol

There total 4 articles about (2S,3S,4R)-1-benzyl-2-[(1R)-1,2-dihydroxyethyl]pyrrolidine-3,4-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:

2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol (3969-61-7) → N-benzyl-1,4-dideoxy-1,4-imino-D-talitol (117781-07-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 4,4-dimethylaminopyridine / pyridine / 2 h / 0 °C

2: 71 percent / 60 h / 60 - 70 °C

3: 50percent aq. trifluoroacetic acid / 24 h / Ambient temperature

With trifluoroacetic acid; dmap; In pyridine;

DOI:10.1016/S0040-4020(01)81717-8

Reference yield:

2,3,5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4) → N-benzyl-1,4-dideoxy-1,4-imino-D-talitol (117781-07-4)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium borohydride / ethanol / 0.5 h / Ambient temperature

2: 4,4-dimethylaminopyridine / pyridine / 2 h / 0 °C

3: 71 percent / 60 h / 60 - 70 °C

4: 50percent aq. trifluoroacetic acid / 24 h / Ambient temperature

With sodium tetrahydroborate; trifluoroacetic acid; dmap; In pyridine; ethanol;

DOI:10.1016/S0040-4020(01)81717-8

Reference yield:

(3aS,4S,6aR)-5-benzyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyrrole (117770-02-2) → N-benzyl-1,4-dideoxy-1,4-imino-D-talitol (117781-07-4)

Guidance literature:

With trifluoroacetic acid; for 24h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)81717-8

upstream raw materials:

(3aS,4S,6aR)-5-benzyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyrrole

2,3,5,6-di-O-isopropylidene-D-mannofuranose

2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol

(R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate