(5R-trans)-5,6-Dihydro-6-((2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy)-5-vinyl-1H,3H-pyrano(3,4-c)pyran-1-one

Base Information

• Chemical Name: (5R-trans)-5,6-Dihydro-6-((2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy)-5-vinyl-1H,3H-pyrano(3,4-c)pyran-1-one
• CAS No.: 11019-08-2
• Molecular Formula: C24H28 O13
• Molecular Weight: 524.479
• European Community (EC) Number: 234-250-9
• DSSTox Substance ID: DTXSID60911527
• Mol file: 11019-08-2.mol

Synonyms:11019-08-2;[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(4-ethenyl-8-oxo-4,6-dihydro-3H-pyrano[3,4-c]pyran-3-yl)oxy]oxan-2-yl]methyl acetate;EINECS 234-250-9;(5R-trans)-5,6-Dihydro-6-((2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy)-5-vinyl-1H,3H-pyrano(3,4-c)pyran-1-one;DTXSID60911527;5-Ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl 2,3,4,6-tetra-O-acetylhexopyranoside

Chemical Property of (5R-trans)-5,6-Dihydro-6-((2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy)-5-vinyl-1H,3H-pyrano(3,4-c)pyran-1-one

Chemical Property:

• Boiling Point: 639°Cat760mmHg
• Flash Point: 272°C
• PSA: 159.19000
• Density: 1.36g/cm³
• LogP: 0.61170
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 12
• Exact Mass: 524.15299094
• Heavy Atom Count: 37
• Complexity: 1010

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC2C(C3=CCOC(=O)C3=CO2)C=C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2C(C3=CCOC(=O)C3=CO2)C=C)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of (5R-trans)-5,6-Dihydro-6-((2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy)-5-vinyl-1H,3H-pyrano(3,4-c)pyran-1-one

There total 4 articles about (5R-trans)-5,6-Dihydro-6-((2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy)-5-vinyl-1H,3H-pyrano(3,4-c)pyran-1-one 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:

2'-O-p-coumaroylgentiopicroside → gentiopicroside tetraacetate (11019-08-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1 N aq. NaOH / methanol / 2 h / 20 °C

2: pyridine / 16 h

With pyridine; sodium hydroxide; In methanol; 1: Hydrolysis / 2: Acetylation;

DOI:10.1248/cpb.47.1338

Reference yield:

acetic anhydride (108-24-7) + gentiopicrin (20831-76-9) → gentiopicroside tetraacetate (11019-08-2)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1016/S0031-9422(00)85059-1

Reference yield:

acetic anhydride (108-24-7) → gentiopicroside tetraacetate (11019-08-2)

Guidance literature:

With pyridine;

upstream raw materials:

acetic anhydride

gentiopicrin

Refernces

• 1、 Kubota,Tomita. "". . p. 1345. Retrieved 1961.