Methyl (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-{2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl}-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate | CAS No. 131189-57-6

Methyl (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-{2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl}-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate

Basic Information

CAS Number

131189-57-6

Molecular Formula

C24H30O14

Molecular Weight

542.49 g/mol

AD

Basic Physical Properties

Physical State

Powder

Solubility

Methanol; Acetontrile; Acetone; Water

COC(=O)C1=COC(C(C1CCOC(=O)C2=CC(=C(C(=C2)O)O)O)C=C)OC3C(C(C(C(O3)CO)O)O)O

InChI

InChI=1S/C24H30O14/c1-3-11-12(4-5-35-21(32)10-6-14(26)17(28)15(27)7-10)13(22(33)34-2)9-36-23(11)38-24-20(31)19(30)18(29)16(8-25)37-24/h3,6-7,9,11-12,16,18-20,23-31H,1,4-5,8H2,2H3/t11-,12+,16-,18-,19+,20-,23+,24+/m1/s1

InChIKey

SMTKSCGLXONVGL-UPIRYGIPSA-N

LogP

-1.0015999999999998

Topological Polar Surface Area

221.89999999999998 Ų

Hydrogen Bond Donor/Acceptor

7 / 14

Complexity

851

Safety Information

View Safety Information

Storage Conditions

2-8℃

Synonyms & References

English

  • 131189-57-6
  • 7-o-galloylsecologanol
  • 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-[2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl]-, methyl ester, (2S,3R,4S)-
  • 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(ss-D-glucopyranosyloxy)-3,4-dihydro-4-[2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl]-, methyl ester, (2S,3R,4S)-
  • comuside
  • AS-78897
  • AC-34772
  • Cornuside
  • NCGC00380868-01_C24H30O14_Methyl (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-{2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl}-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate
  • cor-nuside
  • CHEMBL4872792
  • AKOS030530330
  • 7-galloylsecologanol
  • NCGC00380868-01
  • Cornuside I
  • Methyl (2R,3S,4R)-3-ethenyl-4-[2-(3,4,5-trihydroxybenzoyl)oxyethyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
  • 2H-Pyran-5-carboxylicacid, 3-ethenyl-2-(b-D-glucopyranosyloxy)-3,4-dihydro-4-[2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl]-,methyl ester, (2S,3R,4S)-
  • N1926
  • Y0054
  • Comuside
  • 7-Galloylsecologanol
  • 7-O-Galloylsecologanol
  • (2S)-3α-Ethenyl-2β-(β-D-glucopyranosyloxy)-3,4-dihydro-4α-[2-(galloyloxy)ethyl]-2H-pyran-5-carboxylic acid methyl ester

MDL Number

MFCD21606970

FAQ

What are the physical and chemical properties of Methyl (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-{2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl}-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate (CAS: 131189-57-6)?

The compound is a crystalline solid with a molecular weight of approximately 634.46 g/mol. It is sparingly soluble in water but soluble in common organic solvents. The compound is reactive towards nucleophiles and exhibits acidity. It can form ester bonds and undergo condensation reactions.

How is Methyl (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-{2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl}-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate (CAS: 131189-57-6) typically synthesized?

The compound is typically synthesized via a multi-step approach involving condensation of glucopyranosyl chloride with a vinyl ester, followed by hydroxylation and benzoylation. The use of Lewis acids like aluminium trichloride and catalytic amounts of base is common in the synthesis, providing high yield and good selectivity.

What industries use Methyl (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-{2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl}-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate (CAS: 131189-57-6)?

The compound is used in the pharmaceutical industry for its potential as a drug intermediate. It may also find applications in the production of polymers and sensors due to its chemical reactivity and structural complexity.

What precautions should be taken when handling Methyl (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-{2-[(3,4,5-trihydroxybenzoyl)oxy]ethyl}-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate (CAS: 131189-57-6)?

When handling the compound, gloves, goggles, and a lab coat should be worn to protect against skin and eye contact. It should be stored in a cool, dry place away from heat and open flames. In case of spill, the area should be ventilated and the material handled carefully, following standard chemical safety procedures. Always consult the Safety Data Sheet (SDS) for specific handling instructions.

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