Salireposide

Base Information

• Chemical Name: Salireposide
• CAS No.: 16955-55-8
• Molecular Formula: C20H22 O9
• Molecular Weight: 406.389
• UNII: YUB3J70275
• DSSTox Substance ID: DTXSID60937646
• Metabolomics Workbench ID: 136598
• ChEMBL ID: CHEMBL464611
• Mol file: 16955-55-8.mol

Synonyms:salireposide;16955-55-8;YUB3J70275;Salireposid;UNII-YUB3J70275;CHEMBL464611;DTXSID60937646;CHEBI:137508;AKOS040753905;[5-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl benzoate;XS171863;[2-(Hexopyranosyloxy)-5-hydroxyphenyl]methyl benzoate;Q27294716;beta-D-Glucopyranoside, 2-((benzoyloxy)methyl)-4-hydroxyphenyl;.BETA.-D-GLUCOPYRANOSIDE, 2-((BENZOYLOXY)METHYL)-4-HYDROXYPHENYL;5-hydroxy-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl benzoate

Chemical Property of Salireposide

Chemical Property:

• Vapor Pressure: 3.25E-19mmHg at 25°C
• Melting Point: 206 °C
• Boiling Point: 676.3°Cat760mmHg
• PKA: 9.79±0.20(Predicted)
• Flash Point: 240.5°C
• PSA: 145.91000
• Density: 1.485g/cm³
• LogP: -0.07210
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 406.12638228
• Heavy Atom Count: 29
• Complexity: 524

Purity/Quality:

99% ^*data from raw suppliers

Salireposide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2=C(C=CC(=C2)O)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OCC2=C(C=CC(=C2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

Technology Process of Salireposide

There total 6 articles about Salireposide 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: 71.0%

2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-acetoxybenzyl(3-methoxy-4-acetoxy)benzoate (18265-35-5) → 2-benzoyloxymethyl-4-hydroxyphenyl β-D-glucopyranoside (16955-55-8)

Guidance literature:

With hydrogenchloride; In ethanol; chloroform; water; at 20 ℃; for 48h;

DOI:10.1016/j.carres.2012.10.006

Reference yield:

hydroquinone (123-31-9,8027-02-9) → 2-benzoyloxymethyl-4-hydroxyphenyl β-D-glucopyranoside (16955-55-8)

Guidance literature:

Multi-step reaction with 6 steps

1: acetic acid / 2 h / 110 °C

2: trifluoroacetic acid / 1 h / 80 °C

3: silver(l) oxide / quinoline / 1 h / 20 °C

4: sodium tetrahydroborate; cetyltrimethylammonim bromide / water; chloroform / 2 h / 20 °C

5: pyridine / chloroform / 24 h / 20 °C

6: hydrogenchloride / water; ethanol; chloroform / 48 h / 20 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; cetyltrimethylammonim bromide; acetic acid; trifluoroacetic acid; silver(l) oxide; In quinoline; ethanol; chloroform; water;

DOI:10.1016/j.carres.2012.10.006

Reference yield:

2-hydroxy-5-acetyloxybenzaldehyde (64418-88-8) → 2-benzoyloxymethyl-4-hydroxyphenyl β-D-glucopyranoside (16955-55-8)

Guidance literature:

Multi-step reaction with 4 steps

1: silver(l) oxide / quinoline / 1 h / 20 °C

2: sodium tetrahydroborate; cetyltrimethylammonim bromide / water; chloroform / 2 h / 20 °C

3: pyridine / chloroform / 24 h / 20 °C

4: hydrogenchloride / water; ethanol; chloroform / 48 h / 20 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; cetyltrimethylammonim bromide; silver(l) oxide; In quinoline; ethanol; chloroform; water;

DOI:10.1016/j.carres.2012.10.006

upstream raw materials:

hydroquinone

2-hydroxy-5-acetyloxybenzaldehyde

2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-acetyloxybenzaldehyde

2-(2,3,4,6-tetra-О-acetyl-β-D-glucopyranozyloxy)-5-acetyloxybenzyl alcohol

Refernces