3-(Hexopyranosyloxy)-14-hydroxycard-20(22)-enolide

Base Information

• Chemical Name: 3-(Hexopyranosyloxy)-14-hydroxycard-20(22)-enolide
• CAS No.: 17059-16-4
• Molecular Formula: C29H44 O9
• Molecular Weight: 536.663
• DSSTox Substance ID: DTXSID80937789
• Mol file: 17059-16-4.mol

Synonyms:3beta-(beta-D-Glucopyranosyl)-14-hydroxy-5beta-card-20(22)-enolide;DTXSID80937789;5-beta-CARD-20(22)-ENOLIDE, 3-beta-(beta-D-GLUCOPYRANOSYLOXY)-14-HYDROXY-;LS-52475;3-(Hexopyranosyloxy)-14-hydroxycard-20(22)-enolide

Chemical Property of 3-(Hexopyranosyloxy)-14-hydroxycard-20(22)-enolide

Chemical Property:

• Vapor Pressure: 5.98E-25mmHg at 25°C
• Boiling Point: 735.2°Cat760mmHg
• Flash Point: 239.3°C
• PSA: 145.91000
• Density: 1.36g/cm³
• LogP: 1.42850
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 536.29853298
• Heavy Atom Count: 38
• Complexity: 970

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)OC6C(C(C(C(O6)CO)O)O)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@H]1CCC3C2CC[C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O[C@H]6C(C([C@@H](C(O6)CO)O)O)O

Technology Process of 3-(Hexopyranosyloxy)-14-hydroxycard-20(22)-enolide

There total 21 articles about 3-(Hexopyranosyloxy)-14-hydroxycard-20(22)-enolide 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: 37.0%

Sucrose (57-50-1) + (+)-digitoxigenin (143-62-4) → 3-epi-periplogenin (71884-72-5) + digitoxigenin 3-O-β-D-glucoside (17059-16-4) + periplogenin glucoside (18531-44-7) + 4-[(3S,5S,8R,9S,10R,13R,14S,17S)-5,14-Dihydroxy-10,13-dimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one + (17β)-H-periplogenin (4433-58-3) + periplogenin (514-39-6,4433-58-3,71884-72-5,107596-70-3,117020-71-0)

Guidance literature:

With Tween 80; F₈ cells; In various solvent(s); at 25 ℃; for 360h; Product distribution; other reagents, reaction time;

DOI:10.1016/S0031-9422(97)00748-6

Reference yield: 17.9%

(+)-digitoxigenin (143-62-4) → digitoxigenin 3-O-β-D-glucoside (17059-16-4) + periplogenin glucoside (18531-44-7) + 3α,14-dihydroxy-5β,14β-card-20(22)-enolide (545-52-8) + periplogenin (514-39-6,4433-58-3,71884-72-5,107596-70-3,117020-71-0)

Guidance literature:

With B₂K agar medium; Panax ginseng C_. A_. Meyer cells; In various solvent(s); at 25 ℃; for 456h; Further byproducts given;

DOI:10.1016/0031-9422(96)00079-9

Reference yield: 17.9%

(+)-digitoxigenin (143-62-4) → digitoxigenin 3-O-β-D-glucoside (17059-16-4) + digitoxigenin β-D-sorphoroside + 3α,14-dihydroxy-5β,14β-card-20(22)-enolide (545-52-8) + periplogenin (514-39-6,4433-58-3,71884-72-5,107596-70-3,117020-71-0)

Guidance literature:

With B₂K agar medium; Panax ginseng C_. A_. Meyer cells; In various solvent(s); at 25 ℃; for 456h; Further byproducts given;

DOI:10.1016/0031-9422(96)00079-9

upstream raw materials:

Sucrose

(+)-digitoxigenin

digitoxigenin

Uzarigenin 3-O-β-D-Glucopyranosyl (1-4)-β-D-Glucopyranoside

Downstream raw materials:

β-D-glucose

(+)-digitoxigenin

digitoxigenone

digitoxigenin 3-acetate

Refernces

• 1、 Kawaguchi, Kiichiro,Watanabe, Takashi,Hirotani, Masao,Furuya, Tsutomu. "Biotransformation of digitoxigenin by cultured ginseng cells". . p. 667 - 669. Retrieved 2007/10/03.
• 2、 Hirotani, Masao,Furuya, Tsutomu. "BIOTRANSFORMATION OF DIGITOXIGENIN BY CELL SUSPENSION CULTURES OF DIGITALIS PURPUREA". . p. 531 - 534. Retrieved 2007/10/02.