Fagomine

Base Information

• Chemical Name: Fagomine
• CAS No.: 53185-12-9
• Molecular Formula: C6H13 N O3
• Molecular Weight: 147.174
• Hs Code.: 2933399090
• UNII: 1M10C1P4SM
• DSSTox Substance ID: DTXSID10201243
• Nikkaji Number: J265.072J
• Wikidata: Q21086897
• Metabolomics Workbench ID: 67869
• ChEMBL ID: CHEMBL108084
• Mol file: 53185-12-9.mol

Synonyms:1,2,5-Trideoxy-1,5-imino-D-arabino-hexitol;fagomine

Chemical Property of Fagomine

Chemical Property:

• Vapor Pressure: 3.74E-05mmHg at 25°C
• Melting Point: 185-186℃
• Boiling Point: 315.4°Cat760mmHg
• PKA: 14.16±0.60(Predicted)
• Flash Point: 170.5°C
• PSA: 72.72000
• Density: 1.279g/cm³
• LogP: -1.60880
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 109

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fagomine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(C(C1O)O)CO
• Isomeric SMILES: C1CN[C@@H]([C@H]([C@@H]1O)O)CO
• Description: An alkaloid of Fagopyrum esculentum, fagomine has been characterized as the crystalline hydrochloride with m.p. 176-7°C. The structure has been shown to be that of a trisubstituted pierpidine.
• Uses: Fagomine is an iminosugar which may reduce the risks of developing insulin resistance and becoming overweight. Also lowers blood glucose and modulates bacterial adhesion.

Technology Process of Fagomine

There total 74 articles about Fagomine 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%

6-[(allyloxycarbonyl)amino]-5,6-dideoxy-2-hexulose → D-fagomine (53185-12-9,475630-67-2,637771-88-1)

Guidance literature:

With triethylsilane; palladium on activated charcoal; hydrogen; In ethanol; at 20 ℃;

DOI:10.1039/c1gc15429j

Reference yield: 95.0%

(2R,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate (1430587-89-5) → D-fagomine (53185-12-9,475630-67-2,637771-88-1)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; hydrogen; In ethanol; water; for 12h; Inert atmosphere;

DOI:10.1016/j.tet.2013.03.046

Reference yield: 87.0%

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)piperidine (366815-76-1) → D-fagomine (53185-12-9,475630-67-2,637771-88-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; at 27 ℃; for 12h;

upstream raw materials:

4-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol

1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabinohexitol

(3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose

2-Desoxy-L-threo-5-hexulosonitril

Downstream raw materials:

(2R,3R,4R)-N-benzyloxycarbonyl-2-(((2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)piperidin-1-yl)methyl)-3,4-dihydroxypyrrolidine

Refernces

• 1、 Wei, Mohui,Li, Zijie,Li, Tiehai,Wu, Baolin,Liu, Yunpeng,Qu, Jingyao,Li, Xu,Li, Lei,Cai, Li,Wang, Peng George. "Transforming flask reaction into cell-based synthesis: Production of polyhydroxylated molecules via engineered Escherichia coli". . p. 4060 - 4065. Retrieved 2015/11/11.
• 2、 Min, Im Sook,Kim, Seung In,Hong, Seungmin,Kim, In Su,Jung, Young Hoon. "Total synthesis of d-fagomine and 6-deoxyfagomine". . p. 3901 - 3906. Retrieved 2013/06/27.