3,4-Pyrrolidinediol, 2-(hydroxymethyl)-,(2S,3R,4R)-

Base Information

• Chemical Name: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-,(2S,3R,4R)-
• CAS No.: 105990-42-9
• Molecular Formula: C₅H₁₁NO₃
• Molecular Weight: 133.147
• Mol file: 105990-42-9.mol

Synonyms:(2S,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol;

Chemical Property of 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-,(2S,3R,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-,(2S,3R,4R)-

There total 65 articles about 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-,(2S,3R,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: 100.0%

(2S,3S,4S)-2-benzyloxymethyl-3,4-dibenzyloxy-pyrrolidin (100806-55-1) → (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (52019-89-3,97058-12-3,98632-49-6,100937-51-7,100937-52-8,100937-53-9,105990-40-7,105990-41-8,105990-42-9,129568-47-4,186759-56-8,187339-50-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 10h;

DOI:10.1016/j.tet.2007.02.087

Reference yield: 96.0%

Benzoic acid (2S,3S,4R)-3,4-dihydroxy-5-oxo-pyrrolidin-2-ylmethyl ester (186025-81-0) → (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (52019-89-3,97058-12-3,98632-49-6,100937-51-7,100937-52-8,100937-53-9,105990-40-7,105990-41-8,105990-42-9,129568-47-4,186759-56-8,187339-50-0)

Guidance literature:

With diborane; In tetrahydrofuran; Heating;

DOI:10.1021/jo962028s

Reference yield: 91.0%

(2S,3S,4S)-2-Hydroxymethyl-1-(4-methoxy-benzyl)-pyrrolidine-3,4-diol (245484-08-6) → (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (52019-89-3,97058-12-3,98632-49-6,100937-51-7,100937-52-8,100937-53-9,105990-40-7,105990-41-8,105990-42-9,129568-47-4,186759-56-8,187339-50-0)

Guidance literature:

With formic acid; hydrogen; palladium dihydroxide; In ethanol; for 1h;

DOI:10.1016/S0040-4020(97)00445-6

upstream raw materials:

Benzoic acid (2S,3R,4S)-3,4-dihydroxy-5-oxo-pyrrolidin-2-ylmethyl ester

Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

2-Deoxy-2-[(9-phenylfluoren-9-yl)amino]-3,4-O-isopropylidene-5-methanesulfonyl-D-arabinitol

(2S,3R,4R)-N-(p-toluenesulfonyl)-2-hydroxymethyl-3,4-dihydroxypyrrolidine

Downstream raw materials:

1,4-dideoxy-1,4-imino-L-arabinitol hydrochloride

(2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-([2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy]methyl)pyrrolidine

(2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine

(2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine

Refernces

Palladium(II)-catalyzed highly regio- and diastereoselective cyclization of difunctional allylic N-tosylcarbamates. A convenient synthesis of optically active 4-vinyl-2-oxazolidinones and total synthesis of 1,4-dideoxy-1,4-imino-L-xylitol

10.1021/jo0161429

The study presents a Pd(II)-catalyzed cyclization method for the highly regio- and diastereoselective synthesis of optically active 4-vinyl-2-oxazolidinones from difunctional allylic N-tosylcarbamates, which serves as a convenient approach for the total synthesis of 1,4-dideoxy-1,4-imino-L-xylitol. Key chemicals used in the study include Pd(OAc)2 as the catalyst, LiBr or other halide ions as essential additives, and various homochiral alcohols as substrates. These reagents and substrates are crucial for the cyclization reaction, which involves aminopalladation of alkene and β-heteroatom elimination to regenerate Pd(II) species, yielding the desired 4-vinyl-2-oxazolidinones with high optical activity. The study also explores the mechanism of the reaction and demonstrates the utility of the method through the synthesis of 1,4-dideoxy-1,4-imino-L-xylitol, a potential glycosidase inhibitor.