Digitoxigenin bisdigitoxoside

Base Information

• Chemical Name: Digitoxigenin bisdigitoxoside
• CAS No.: 16479-50-8
• Molecular Formula: C35H54 O10
• Molecular Weight: 634.808
• European Community (EC) Number: 240-533-8
• ChEMBL ID: CHEMBL1651623
• Metabolomics Workbench ID: 198969
• Nikkaji Number: J55.405G
• Mol file: 16479-50-8.mol

Synonyms:digitoxigenin-bis(digitoxoside);DT-BIS(DT)

Chemical Property of Digitoxigenin bisdigitoxoside

Chemical Property:

• Vapor Pressure: 3.71E-29mmHg at 25°C
• Boiling Point: 794.1°C at 760 mmHg
• Flash Point: 246.7°C
• Density: 1.3g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 634.37169792
• Heavy Atom Count: 45
• Complexity: 1160

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2C(OC(CC2O)OC3CCC4(C(C3)CCC5C4CCC6(C5(CCC6C7=CC(=O)OC7)O)C)C)C)O)O
• Isomeric SMILES: C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)O[C@H]3CC[C@]4([C@@H](C3)CC[C@@H]5[C@@H]4CC[C@]6([C@@]5(CC[C@@H]6C7=CC(=O)OC7)O)C)C)C)O)O

Technology Process of Digitoxigenin bisdigitoxoside

There total 10 articles about Digitoxigenin bisdigitoxoside 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: 90.0%

digitoxin (71-63-6) → digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside) (16479-50-8)

Guidance literature:

digitoxin; With sodium periodate; In ethanol; water;

With sodium tetrahydroborate; ethanol; for 4h;

With hydrogenchloride; In methanol; water;

DOI:10.1055/s-0043-109557

Reference yield: 82.0%

digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside) (30788-61-5) → digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside) (16479-50-8)

Guidance literature:

With lithium hydroxide; In methanol; water; at 20 ℃; for 3h;

DOI:10.1021/ol061683b

Reference yield:

digitoxin (71-63-6) → digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside) (16479-50-8) + β-D-digitoxosyl-(1<*>4)-β-D-digitoxose (90762-99-5,90763-00-1,90763-10-3,90790-04-8) + evatromonoside (18404-43-8) + (+)-digitoxigenin (143-62-4)

Guidance literature:

With water; In 1,4-dioxane; at 100 ℃; for 35h; Further byproducts given;

upstream raw materials:

digitoxin

digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside)

digitoxigen 3-O-acetyl-2,6-dideoxy-4-O-((2'R,6'R)-3',6'-dihydro-6'-methyl-2H-pyran-2'-yl)-β-D-ribo-hexopyranoside

Downstream raw materials:

evatromonoside

Refernces

• 1、 Zhou, Maoquan,O'Doherty, George A.. "A stereoselective synthesis of digitoxin and digitoxigen mono- and bisdigitoxoside from digitoxigenin via a palladium-catalyzed glycosylation". . p. 4339 - 4342. Retrieved 2006.
• 2、 Zhou, Maoquan,O'Doherty, George A.. "De novo approach to 2-deoxy-β-glycosides: Asymmetric syntheses of digoxose and digitoxin". . p. 2485 - 2493. Retrieved 2008/02/02.