(2S,3S,4R)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol

Base Information

• Chemical Name: (2S,3S,4R)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol
• CAS No.: 117770-04-4
• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.272
• Mol file: 117770-04-4.mol

Synonyms:3,4-Pyrrolidinediol,2-(hydroxymethyl)-1-(phenylmethyl)-, [2S-(2a,3b,4b)]-; N-Benzyl-1,4-dideoxy-1,4-imino-L-ribitol

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

Chemical Property:

• Vapor Pressure: 1.79E-07mmHg at 25°C
• Boiling Point: 410.5°C at 760 mmHg
• Flash Point: 230.7°C
• Density: 1.308g/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-(hydroxymethyl)pyrrolidine-3,4-diol

There total 4 articles about (2S,3S,4R)-1-benzyl-2-(hydroxymethyl)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: 90.0%

→ N-benzyl-1,4-dideoxy-1,4-imino-L-ribitol (117770-04-4)

Guidance literature:

Reference yield:

(2S,3S,4R)-N-benzyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol (117858-82-9) → N-benzyl-1,4-dideoxy-1,4-imino-L-ribitol (117770-04-4)

Guidance literature:

With trifluoroacetic acid; for 20h; Ambient temperature;

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

Reference yield:

(S)-1-((3aS,4S,6aR)-5-benzyl-2,2-dimethyltetrahydro-4H-[1,3] dioxolo[4,5-c]pyrrol-4-yl)ethane-1,2-diol (117781-06-3) → N-benzyl-1,4-dideoxy-1,4-imino-L-ribitol (117770-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium periodate, 2.) sodium borohydride / 1.) 80percent aq. ethanol, room temp., 30 min, 2.) 80percent aq. ethanol, room temp., 60 min

2: 50percent aq. trifluoroacetic acid / 20 h / Ambient temperature

With sodium tetrahydroborate; sodium periodate; trifluoroacetic acid;

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

upstream raw materials:

(2S,3S,4R)-N-benzyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol

(S)-1-((3aS,4S,6aR)-5-benzyl-2,2-dimethyltetrahydro-4H-[1,3] dioxolo[4,5-c]pyrrol-4-yl)ethane-1,2-diol

(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