Bakankoside

Base Information

• Chemical Name: Bakankoside
• CAS No.: 1398-17-0
• Molecular Formula: C16H23NO8
• Molecular Weight: 357.36
• UNII: 0JKT0DM566
• DSSTox Substance ID: DTXSID10331852
• Nikkaji Number: J14.362F
• Wikidata: Q27105908
• Metabolomics Workbench ID: 69342
• Mol file: 1398-17-0.mol

Synonyms:Bakankoside;Bakankosin;Bakankosine;Bakankosin [MI];1398-17-0;bacancosin;UNII-0JKT0DM566;0JKT0DM566;C09914;H-Pyrano(3,4-C)pyridin-8-one, 4-ethenyl-3-(beta-D-glucopyranosyloxy)-3,4,4a,5,6,7-hexahydro-, (3S,4R,4aS)-;AC1L9CYZ;CHEBI:2983;SCHEMBL21807732;DTXSID10331852;(3S,4R,4aS)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,4a,5,6,7-hexahydropyrano[3,4-c]pyridin-8-one;Q27105908;(3S)-4alpha-Vinyl-3-beta-D-glucopyranosyloxy-3,4,4abeta,5,6,7-hexahydro-8H-pyrano[3,4-c]pyridin-8-one;(3S,4R,4aS)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4-vinyl-3,4,4a,5,6,7-hexahydropyrano[3,4-c]pyridin-8-one;(3S,4R,4aS)-4-Ethenyl-3-(beta-D-glucopyranosyloxy)-3,4,4a,5,6,7-hexahydro-8H-pyrano[3,4-c]pyridin-8-one;8H-Pyrano[3,4-c]pyridin-8-one, 4-ethenyl-3-(.beta.-D-glucopyranosyloxy)-3,4,4a,5,6,7-hexahydro-, [3S-(3.alpha.,4.beta.,4a.alpha.)]-;H-PYRANO(3,4-C)PYRIDIN-8-ONE, 4-ETHENYL-3-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,4,4A,5,6,7-HEXAHYDRO-, (3S,4R,4AS)-

Chemical Property of Bakankoside

Chemical Property:

• Vapor Pressure: 3.74E-20mmHg at 25°C
• Boiling Point: 658.8°C at 760 mmHg
• Flash Point: 352.2°C
• PSA: 141.20000
• Density: 1.47g/cm³
• LogP: -1.74270
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 357.14236669
• Heavy Atom Count: 25
• Complexity: 552

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1C2CCNC(=O)C2=COC1OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C=C[C@@H]1[C@@H]2CCNC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

Technology Process of Bakankoside

There total 6 articles about Bakankoside 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%

bakankosin tetraacetate (60393-49-9) → bakankosin (1398-17-0)

Guidance literature:

With sodium ethanolate; In methanol; for 6h; Ambient temperature;

DOI:10.1016/0040-4020(89)80097-3

Reference yield:

(4S,5R,6S)-4-(2-Iodo-ethyl)-6-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester (77870-37-2) → bakankosin (1398-17-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / sodium azide / dimethylformamide / 12 h / Ambient temperature

2: 89 percent / triethylamine, propanedithiol / methanol / 20 h / Ambient temperature

3: 90 percent / sodium ethanolate / methanol / 6 h / Ambient temperature

With sodium azide; 1,2-propanedithiol; sodium ethanolate; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(89)80097-3

Reference yield:

C27H39IO13Si → bakankosin (1398-17-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / diethyl ether

2: 65 percent / sodium azide / dimethylformamide / 12 h / Ambient temperature

3: 89 percent / triethylamine, propanedithiol / methanol / 20 h / Ambient temperature

4: 90 percent / sodium ethanolate / methanol / 6 h / Ambient temperature

With sodium azide; 1,2-propanedithiol; sodium ethanolate; triethylamine; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(89)80097-3

upstream raw materials:

secologanin

bakankosin tetraacetate

(4S,5R,6S)-4-(2-Iodo-ethyl)-6-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

Downstream raw materials:

Dihydrobakankosin