Kelampayoside A

Base Information

• Chemical Name: Kelampayoside A
• CAS No.: 87562-76-3
• Molecular Formula: C20H30O11
• Molecular Weight: 478.45
• DSSTox Substance ID: DTXSID101317142
• Nikkaji Number: J739.935I
• Wikidata: Q27137315
• Metabolomics Workbench ID: 125445
• ChEMBL ID: CHEMBL1923077
• Mol file: 87562-76-3.mol

Synonyms:kelampayoside A

Chemical Property of Kelampayoside A

Chemical Property:

• Boiling Point: 685.6 °C at 760 mmHg
• Flash Point: 368.4 °C
• PSA: 185.99000
• Density: 1.41 g/cm³
• LogP: -2.64400
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 9
• Exact Mass: 478.16864101
• Heavy Atom Count: 33
• Complexity: 597

Purity/Quality:

98%min ^*data from raw suppliers

KelampayosideA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)OC2C(C(C(C(O2)COC3C(C(CO3)(CO)O)O)O)O)O
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@](CO3)(CO)O)O)O)O)O

Technology Process of Kelampayoside A

There total 9 articles about Kelampayoside A 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: 91.0%

3,4,5-trimethoxyphenyl 6-O-(5-O-benzyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside (209113-72-4) → kelampayoside A (87562-76-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In isopropyl alcohol;

DOI:10.1016/S0040-4039(98)00673-X

Reference yield:

ethyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (35784-51-1) → kelampayoside A (87562-76-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / triflic acid; N-iodosuccinimide / 1,2-dichloro-ethane; diethyl ether / 0.03 h / 0 °C

2: N-iodosuccinimide; triflic acid / CH₂Cl₂; H₂O / 20 °C

3: Cs₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

4: 63 percent / BF₃*OEt₂ / CH₂Cl₂; tetrahydrofuran / 0.5 h / 20 °C

5: 88 percent / MeONa / methanol; CH₂Cl₂ / 2 h / 20 °C

6: 91 percent / H₂ / Pd/C / propan-2-ol; H₂O / 12 h / 20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen; sodium methylate; caesium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; isopropyl alcohol; 1: Condensation / 2: desulfation / 3: Condensation / 4: Condensation / 5: Hydrolysis / 6: Hydrogenolysis;

DOI:10.1016/S0040-4020(99)00527-X

Reference yield:

3,4,5-trimethoxyphenyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-β-D-glucopyranoside (209113-70-2) → kelampayoside A (87562-76-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / MeONa / methanol; CH₂Cl₂ / 2 h / 20 °C

2: 91 percent / H₂ / Pd/C / propan-2-ol; H₂O / 12 h / 20 °C

With hydrogen; sodium methylate; palladium on activated charcoal; In methanol; dichloromethane; water; isopropyl alcohol; 1: Hydrolysis / 2: Hydrogenolysis;

DOI:10.1016/S0040-4020(99)00527-X

upstream raw materials:

3,4,5-trimethoxyphenyl 6-O-(5-O-benzyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

3,4,5-trimethoxyphenol

ethyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

3,4,5-trimethoxyphenyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-β-D-glucopyranoside

Refernces

• 1、 Duynstee, Howard I.,De Koning, Martijn C.,Van Der Marel, Gijs A.,Van Boom, Jacques H.. "Synthesis of 3,4,5-trimethoxyphenyl 5-O-caffeoyl-β-D-erythro- apiofuranosyl-(1→6)-β D-glucopyranoside: Kelampayoside B". . p. 4129 - 4132. Retrieved 2007/10/03.