(2S,3R,4R,5S)-2,5-Bis(hydroxymethyl)pyrrolidine-3,4-diol

Base Information

• Chemical Name: (2S,3R,4R,5S)-2,5-Bis(hydroxymethyl)pyrrolidine-3,4-diol
• CAS No.: 105015-44-9
• Molecular Formula: C6H13 N O4
• Molecular Weight: 163.174
• Hs Code.: 2933990090
• European Community (EC) Number: 640-237-2
• Nikkaji Number: J2.279.574K
• Mol file: 105015-44-9.mol

Synonyms:105015-44-9;(2S,3R,4R,5S)-2,5-Bis(hydroxymethyl)pyrrolidine-3,4-diol;(2S,5S)-BISHYDROXYMETHYL-(3R,4R)-BISHYDROXYPYRROLIDINE;SCHEMBL19745374;PFYHYHZGDNWFIF-UNTFVMJOSA-N;AKOS027384409;J-001332;Z1255487781;(2S)-2beta,5alpha-Bis(hydroxymethyl)pyrrolidine-3beta,4alpha-diol

Chemical Property of (2S,3R,4R,5S)-2,5-Bis(hydroxymethyl)pyrrolidine-3,4-diol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 161-162°C
• Refractive Index: 1.559
• Boiling Point: 395.893°C at 760 mmHg
• Flash Point: 221.909°C
• PSA: 92.95000
• Density: 1.408g/cm³
• LogP: -2.63800
• Storage Temp.: -20°C Freezer
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 163.08445790
• Heavy Atom Count: 11
• Complexity: 118

Purity/Quality:

98%Min ^*data from raw suppliers

(2S,5S)-Bishydroxymethyl-(3R,4R)-bishydroxypyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(N1)CO)O)O)O
• Isomeric SMILES: C([C@H]1[C@H]([C@@H]([C@@H](N1)CO)O)O)O
• Uses: A potent and specific glycosidase inhibitor. Shows potential as an antiviral agent A potent and specific glycosidase inhibitor. Shows potential as an antiviral agent.

Technology Process of (2S,3R,4R,5S)-2,5-Bis(hydroxymethyl)pyrrolidine-3,4-diol

There total 17 articles about (2S,3R,4R,5S)-2,5-Bis(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,3R,4R,5S)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)pyrrolidine (881185-77-9) → (2S,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidine (105015-44-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 30 ℃; for 13h;

DOI:10.1016/j.tet.2005.11.037

Reference yield: 100.0%

N-benzyl-3,4-di-O-benzyl-2,5-dideoxy-2,5-imino-L-iditol (176166-99-7) → (2S,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidine (105015-44-9)

Guidance literature:

With hydrogen; acetic acid; palladium; for 18h;

DOI:10.1016/S0968-0896(96)00266-0

Reference yield: 88.0%

2,3:4,5-di-O-benzylidene-(3R,4R)-dihydroxy-(2S,5S)-bis(hydroxymethyl)pyrrolidine (111248-47-6,133443-76-2,187343-15-3) → (2S,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidine (105015-44-9)

Guidance literature:

With trifluoroacetic acid; In water; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86097-X

upstream raw materials:

2,3:4,5-di-O-benzylidene-(3R,4R)-dihydroxy-(2S,5S)-bis(hydroxymethyl)pyrrolidine

(2S,3R,4R,5S)-1-Benzyl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol; hydrochloride

N-benzyl-3,4-di-O-benzyl-2,5-dideoxy-2,5-imino-L-iditol

5-azido-5-deoxy-L-sorbose