Nectrisine

Base Information

• Chemical Name: Nectrisine
• CAS No.: 108692-47-3
• Molecular Formula: C₅H₉NO₃
• Molecular Weight: 131.131
• DSSTox Substance ID: DTXSID80910830
• Wikidata: Q76010332
• Metabolomics Workbench ID: 161052
• Mol file: 108692-47-3.mol

Synonyms:3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine;3,4-dihydroxy-5-hydroxymethyl-1-pyrroline;FR 900483;FR-900483;nectrisine

Chemical Property of Nectrisine

Chemical Property:

• Vapor Pressure: 5.76E-06mmHg at 25°C
• Boiling Point: 340.3°Cat760mmHg
• Flash Point: 211°C
• Density: 1.62g/cm³
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 131.058243149
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(C(C1O)O)CO
• Isomeric SMILES: C1=N[C@@H]([C@H]([C@H]1O)O)CO

Technology Process of Nectrisine

There total 15 articles about Nectrisine 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: 96.0%

2,2,2-Trifluoro-1-((3S,4R,5R)-2,3,4-trihydroxy-5-hydroxymethyl-pyrrolidin-1-yl)-ethanone (397242-81-8) → (2R,3R,4R)-2-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol (108692-47-3)

Guidance literature:

2,2,2-Trifluoro-1-((3S,4R,5R)-2,3,4-trihydroxy-5-hydroxymethyl-pyrrolidin-1-yl)-ethanone; With sodium hydroxide; In water; at 20 ℃; for 0.5h;

With acetic acid; pH=4;

DOI:10.1016/S0040-4039(01)01684-7

Reference yield: 96.0%

4-deoxy-3-O-formyl-4-trifluoroacetamido-D-arabinose → (2R,3R,4R)-2-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol (108692-47-3)

Guidance literature:

With sodium hydroxide; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.39.2807

Reference yield: 80.0%

3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (627860-02-0) → (2R,3R,4R)-2-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol (108692-47-3)

Guidance literature:

3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester; With hydrogenchloride; In tetrahydrofuran; at 50 ℃; for 2h;

With Dowex 1X₂ (HO^1-); In water;

DOI:10.1016/j.tetlet.2003.08.030

upstream raw materials:

Acetic acid (3S,4R,5R)-3,4-bis-benzyloxy-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yl ester

3-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucose

4-amino-4-deoxy-L-arabinopyranose hydrochloride

2,2,2-Trifluoro-1-((3S,4R,5R)-2,3,4-trihydroxy-5-hydroxymethyl-pyrrolidin-1-yl)-ethanone

Downstream raw materials:

2,3-di-O-benzoyl-1,4-dideoxy-1,4-imino-D-arabinitol

2,3,5-tri-O-acetyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol

2,3-di-O-benzoyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol

N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-5-O-triphenylmethyl-D-arabinitol