Valiolamine

Base Information

• Chemical Name: Valiolamine
• CAS No.: 83465-22-9
• Molecular Formula: C7H15NO5
• Molecular Weight: 193.2
• Hs Code.: 2922199090
• European Community (EC) Number: 617-461-4
• DSSTox Substance ID: DTXSID601003447
• Nikkaji Number: J126.275K
• Wikidata: Q72516036
• Pharos Ligand ID: 8YGP6VA88FLF
• Metabolomics Workbench ID: 98375
• ChEMBL ID: CHEMBL222396
• Mol file: 83465-22-9.mol

Synonyms:epivaliolamine;valiolamine

Chemical Property of Valiolamine

Chemical Property:

• Boiling Point: 368.6 °C at 760 mmHg
• PKA: 13.27±0.70(Predicted)
• Flash Point: 176.7 °C
• PSA: 72.27000
• Density: 1.623 g/cm³
• LogP: 0.30140
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Sparingly)
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 193.09502258
• Heavy Atom Count: 13
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

Valiolamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(C1(CO)O)O)O)O)N
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]([C@]1(CO)O)O)O)O)N
• Uses: Valiolamine is a aminocyclitol that exhibits potent alpha-D-glucosidase inhibitory activity against porcine intestinal sucrase, maltase and isomaltase.

Technology Process of Valiolamine

There total 67 articles about Valiolamine 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: 95.3%

C22H39NO7 → (1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane (83465-22-9)

Guidance literature:

With cesium hydroxide octahydrate; In tetrahydrofuran; water; for 3h; Reflux;

Reference yield: 95.0%

1L-(1,2,4,5/3)-5-acetamido-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-1,2,3,4-cyclohexanetetrol → (1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane (83465-22-9)

Guidance literature:

With water; barium(II) hydroxide; at 80 ℃; for 8h; Reagent/catalyst; Time;

DOI:10.1016/j.tet.2013.06.046

Reference yield: 95.0%

(1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane (1054636-37-1) → (1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane (83465-22-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; water; at 20 ℃; for 24h;

DOI:10.1002/ejoc.201300804

upstream raw materials:

2,3,4-tri-O-benzyl-5-amino-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol

<1S-(endo,exo,endo)>-6,7,8-trihydroxy-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo<3.3.1>nonane

1-(bromomethyl)-6,7,8-trihydroxy-3-oxo-2-oxa-4-azabicyclo<3.3.1>nonane

6,7,8-triacetoxy-1-(bromomethyl)-3-oxo-2-oxa-4-azabicyclo<3.3.1>nonane

Downstream raw materials:

N-(3-pyridylmethyl)valiolamine

N-thenylvaliolamine

N-<(S)-α-(hydroxymethyl)benzyl>valiolamine

N-<(R)-α-(hydroxymethyl)benzyl>valiolamine