10-Deoxysarpagine

Base Information

• Chemical Name: 10-Deoxysarpagine
• CAS No.: 604-99-9
• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 294.396
• UNII: 8RD788YSD2
• DSSTox Substance ID: DTXSID001317620
• Metabolomics Workbench ID: 50360,131357
• Wikidata: Q105298751
• Wikipedia: Tombozine,Normacusine B,Normacusine_B
• Mol file: 604-99-9.mol

Synonyms:Tombozine;10-Deoxysarpagine;Normacusine B;604-99-9;Vellosiminol;Sarpagan-17-ol;DTXSID001317620;AKOS040763096

Chemical Property of 10-Deoxysarpagine

Chemical Property:

• Vapor Pressure: 9.65E-10mmHg at 25°C
• Refractive Index: 1.705
• Boiling Point: 472.7 °C at 760 mmHg
• Flash Point: 239.7 °C
• PSA: 39.26000
• Density: 1.3g/cm³
• LogP: 2.96190
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 294.173213330
• Heavy Atom Count: 22
• Complexity: 490

Purity/Quality:

98%min ^*data from raw suppliers

Tombozine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CN2C3CC1C(C2CC4=C3NC5=CC=CC=C45)CO
• Isomeric SMILES: C/C=C\1/CN2[C@H]3C[C@@H]1[C@H]([C@@H]2CC4=C3NC5=CC=CC=C45)CO
• Description: This carboline alkaloid has been isolated from the stem bark of Strychnos nedeola and the trunk bark of Tabernaernontana brachyantha. The structure has been established on the basis of spectroscopic evidence.

Technology Process of 10-Deoxysarpagine

There total 86 articles about 10-Deoxysarpagine 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: 95.0%

(+)-3-ethylidene-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methanoindolo[2,3-a]quinolizine-13-carboxaldehyde (6874-98-2) → (+)-3-ethylidene-1,3,4,7,12,12b-hexahydro-13-hydroxymethyl-2H,6H-2,6-methanoindolo[2,3-a]quinolizine (1358-75-4,119241-70-2,119241-73-5,124096-81-7,126640-98-0,604-99-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol;

DOI:10.1021/ol0101990

Reference yield: 95.0%

(Z)-(+)-(16S)-12-benzyl-10-desoxy-18-hydroxysarpagine (119184-33-7,129784-68-5) → (+)-koumidine (604-99-9,1358-75-4,119241-70-2,119241-73-5,124096-81-7,126640-98-0)

Guidance literature:

With ammonia; sodium; at -30 ℃; for 1h;

DOI:10.1021/ja00169a033

Reference yield: 36.0%

2-[(2R,6R,12bR)-12-Benzyl-13-hydroxymethyl-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-ethanol (119184-33-7,129784-68-5) → 18-hydroxydeoxysarpagine (119184-34-8,128572-25-8,129784-69-6) + E-koumidine (604-99-9,1358-75-4,119241-70-2,119241-73-5,124096-81-7,126640-98-0)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -30 ℃;

DOI:10.1021/ja00184a086

upstream raw materials:

16-epi-Vellosimine

(Z)-(+)-(16S)-12-benzyl-10-desoxy-18-hydroxysarpagine

(6R,10R)-(+)-5-benzyl-9-oxo-12-(prop-2-ynyl)-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

(S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester

Downstream raw materials:

Sarpagine

(+)-taberpsychine

(19Z)-taberpsychine

(+)-taberpsychine

Refernces

• 1、 Yu, Jianming,Wang, Tao,Liu, Xiaoxiang,Deschamps, Jeffrey,Flippen-Anderson, Judith,Liao, Xuebin,Cook, James M.. "General approach for the synthesis of sarpagine indole alkaloids. Enantiospecific total synthesis of (+)-vellosimine, (+)-normacusine B, (-)-alkaloid Q3, (-)-panarine, (+)-Na-methylvellosimine, and (+)-Na-methyl-16-epipericyclivine". . p. 7565 - 7581. Retrieved 2007/10/03.
• 2、 Yu, Bingwu,Ruppert, Martin,Stoeckigt, Joachim. "Deoxysarpagine hydroxylase--a novel enzyme closing a short side pathway of alkaloid biosynthesis in Rauvolfia.". . p. 2479 - 2483. Retrieved 2007/10/03.