Salacinol

Base Information

• Chemical Name: Salacinol
• CAS No.: 200399-47-9
• Molecular Formula: C9H18O9S2
• Molecular Weight: 334.369
• Wikidata: Q110185891
• Pharos Ligand ID: 69T67384K97T
• ChEMBL ID: CHEMBL239249,CHEMBL1208974
• Mol file: 200399-47-9.mol

Synonyms:neosalacinol;salacinol

Chemical Property of Salacinol

Chemical Property:

• PSA: 218.98000
• LogP: -3.45510
• XLogP3: -3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 334.03922449
• Heavy Atom Count: 20
• Complexity: 381

Purity/Quality:

99%, ^*data from raw suppliers

Salacinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(C([S+]1CC(C(CO)OS(=O)(=O)[O-])O)CO)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([S+]1C[C@H]([C@H](CO)OS(=O)(=O)[O-])O)CO)O)O
• Uses: SALACINOLEXTRACT is a α-glucosidase inhibitor discovered from the herb, Salacia reticulata. Salacinol is used as an antidiabetic agent. Salacinol is a α-glucosidase inhibitor discovered from the herb, Salacia reticulata. Salacinol is used as an antidiabetic agent.

Technology Process of Salacinol

There total 19 articles about Salacinol 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: 86.0%

2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-{[(2S,3S)-2,4-benzylidenedioxy-3-(sulfooxy)butyl]-episulfoniumylidene}-D-arabinitol inner salt → (2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate (200399-47-9)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 0.5h;

DOI:10.1055/s-2003-40353

Reference yield: 82.0%

2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol (942610-80-2) → (2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate (200399-47-9)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; at 50 ℃; for 5h;

DOI:10.1016/j.bmc.2006.10.014

Reference yield: 74.0%

1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol (438576-21-7) → (2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate (200399-47-9)

Guidance literature:

With hydrogenchloride; at 40 ℃; for 4h;

DOI:10.1016/j.bmc.2006.10.014

upstream raw materials:

1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol

2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol

3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose

1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol

Refernces

• 1、 -. "Compound useful for producing [...] and their production, production of [...], diol protecting group of deprotection method and method, as well as diol protecting groups (by machine translation)". . . Retrieved 2019/01/06.
• 2、 -. "COMPOUND USEFUL FOR MANUFACTURING SALACINOL, METHOD FOR MANUFACTURING THE COMPOUND, METHOD FOR MANUFACTURING SALACINOL, METHODS FOR PROTECTING AND DEPROTECTING DIOL GROUP, AND PROTECTIVE AGENT FOR DIOL GROUP". . . Retrieved 2017/01/23.