2-(Hydroxymethyl)pyrrolidine-3,4-diol

Base Information

• Chemical Name: 2-(Hydroxymethyl)pyrrolidine-3,4-diol
• CAS No.: 105990-41-8
• Molecular Formula: C5H11 N O3
• Molecular Weight: 133.147
• Nikkaji Number: J921.329E
• Wikidata: Q105196741
• Metabolomics Workbench ID: 48553
• Mol file: 105990-41-8.mol

Synonyms:2-(hydroxymethyl)pyrrolidine-3,4-diol;100937-52-8;2-HYDROXYMETHYL-PYRROLIDINE-3,4-DIOL;2-(Hydroxymethyl)-(2R-(2a,3b,4b))-3,4-Pyrrolidinediol;2-(Hydroxymethyl)-[2R-(2a,3b,4b)]-3,4-Pyrrolidinediol;D06KVV;SCHEMBL981088;1,4-dideoxy-1,4-iminopentitol;OQEBIHBLFRADNM-UHFFFAOYSA-N;HMS3373I18;IMR;3,4-Dihydroxy-2-pyrrolidinemethanol;3,4-dihydroxy-2-hydroxymethylpyrrolidine;(+)-1,4-Dideoxy-1,4-imino-D-ribitol;2-(Hydroxymethyl)-(2R,3R,4S)-3,4-Pyrrolidinediol;188925-57-7

Chemical Property of 2-(Hydroxymethyl)pyrrolidine-3,4-diol

Chemical Property:

• Vapor Pressure: 2.84E-05mmHg at 25°C
• Boiling Point: 319.1°Cat760mmHg
• PKA: 14.13±0.60(Predicted)
• Flash Point: 188.8°C
• PSA: 72.72000
• Density: 1.368g/cm³
• LogP: -1.99890
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 133.07389321
• Heavy Atom Count: 9
• Complexity: 98.2

Purity/Quality:

99%min ^*data from raw suppliers

1,4-Dideoxy-1,4-imino-D-ribitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(N1)CO)O)O

Technology Process of 2-(Hydroxymethyl)pyrrolidine-3,4-diol

There total 60 articles about 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: 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:

(2S,3S,4S)-2-benzyloxymethyl-3,4-dibenzyloxy-pyrrolidin

1-azido-1-deoxy-4-O-methanesulphonyl-2,3,5-tri-O-benzyl-D-xylitol

methyl 4-azido-4-deoxy-β-L-arabinopyranoside

(2S,3S,4S)-2-Hydroxymethyl-1-(4-methoxy-benzyl)-pyrrolidine-3,4-diol

Downstream raw materials:

3,5-di-O-benzyl-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2-O-methoxymethyl-D-ribitol

(2R,3R)-2,2,2-trichloroethyl-3-(benzyloxy)-2-(benzyloxymethyl)-4-oxopyrrolidine-1-carboxylate¹

3,5-di-O-benzyl-1,4-dideoxy-1,4-imino-N-(2,2,2-trichloroethoxycarbonyl)-D-ribitol

(2S,3S,4S)-3,4-dihydroxy-2-hydroxymethyl-1-methylpyrrolidine

Refernces

• 1、 -. "METHODS OF TREATING POMPE DISEASE". Paragraph 0061-0062. . Retrieved 2021/04/10.
• 2、 Glawar,Martínez,Ayers,Hollas,Ngo,Nakagawa,Kato,Butters,Fleet,Jenkinson. "Structural essentials for β-: N -acetylhexosaminidase inhibition by amides of prolines, pipecolic and azetidine carboxylic acids". . p. 10371 - 10385. Retrieved 2016/11/18.