Ramnodigin

Base Information

• Chemical Name: Ramnodigin
• CAS No.: 33156-28-4
• Molecular Formula: C₂₉H₄₄O₆
• Molecular Weight: 488.665
• UNII: Z8SRY7BR30
• ChEMBL ID: CHEMBL1651649
• DSSTox Substance ID: DTXSID301043347
• Metabolomics Workbench ID: 199369
• NCI Thesaurus Code: C76589
• Nikkaji Number: J17.797K
• Mol file: 33156-28-4.mol

Synonyms:Ramnodigin;33156-28-4;Ramnodigin [INN];Z8SRY7BR30;3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[(2R,5R,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one;Ramnodiginum;UNII-Z8SRY7BR30;SCHEMBL1812161;CHEMBL1651649;DTXSID301043347;14-Hydroxy-3beta-((2,3,6-trihydroxy-alpha-L-erythro-hexopyranosyl)oxy)-5beta-card-20(22)-enolide;Q27295149;14-Hydroxy-3beta-((2,3,6-trideoxy-alpha-L-erythro-hexopyranosyl)oxy)-5beta-Card-20(22)-enolide

Chemical Property of Ramnodigin

Chemical Property:

• Vapor Pressure: 1.89E-19mmHg at 25°C
• Boiling Point: 646.6°Cat760mmHg
• Flash Point: 209.4°C
• PSA: 85.22000
• Density: 1.22g/cm³
• LogP: 4.51450
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 488.31378912
• Heavy Atom Count: 35
• Complexity: 886

Purity/Quality:

99% ^*data from raw suppliers

RAMNODIGIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(CCC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)O
• Isomeric SMILES: C[C@H]1[C@@H](CC[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)C)O

Technology Process of Ramnodigin

There total 9 articles about Ramnodigin 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%

C29H42O6 (33156-32-0) → 3β-(2',3'-Didesoxy-α-L-rhamnopyranosyloxy)digitoxigenin (33156-28-4)

Guidance literature:

With 4-methyl-morpholine; 2-nitrobenzenesulfonyl hydrazide; triethylamine; at 0 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/ml100219d

Reference yield: 80.0%

Acetic acid (2S,3R,6R)-6-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydro-furan-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester (33156-27-3) → 3β-(2',3'-Didesoxy-α-L-rhamnopyranosyloxy)digitoxigenin (33156-28-4)

Guidance literature:

With potassium hydrogencarbonate; In methanol; water; for 0.416667h; Heating;

Reference yield:

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate (865484-73-7) → 3β-(2',3'-Didesoxy-α-L-rhamnopyranosyloxy)digitoxigenin (33156-28-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine / tetrahydrofuran; dichloromethane / 6 h / 0 °C / Inert atmosphere

2: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 1 h / -78 °C

3: 4-methyl-morpholine; 2-nitrobenzenesulfonyl hydrazide; triethylamine / 8 h / 0 - 20 °C / Inert atmosphere

With 4-methyl-morpholine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; cerium(III) chloride; 2-nitrobenzenesulfonyl hydrazide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2: Luche reduction;

DOI:10.1021/ml100219d

upstream raw materials:

Acetic acid (2S,3R,6R)-6-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydro-furan-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

(Digitoxigenin-3-yl)-4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

1-(2-furyl)-1-ethanone

Refernces

• 1、 Wang, Hua-Yu Leo,Xin, Wenjun,Zhou, Maoquan,Stueckle, Todd A.,Rojanasakul, Yon,O'Doherty, George A.. "Stereochemical survey of digitoxin monosaccharides". . p. 73 - 78. Retrieved 2011/04/17.
• 2、 Stache, Ulrich,Radscheit, Kurt,Haede, Werner,Fritsch, Werner. "3β-2',3'-Didesoxy-α,L-rhamnopyranoside von Cardenoliden". . p. 560 - 561. Retrieved 2007/10/02.