16-Hydroxytabersonine

Base Information

Chemical Name:16-Hydroxytabersonine
CAS No.:22149-28-6
Molecular Formula:C21H24 N2 O3
Molecular Weight:352.433
Hs Code.:
UNII:GV2G76UPD2
DSSTox Substance ID:DTXSID601032123
Nikkaji Number:J1.309.174I
Wikipedia:16-Hydroxytabersonine
Wikidata:Q20179989
Metabolomics Workbench ID:51006
ChEMBL ID:CHEMBL2011510

Synonyms:11-Hydroxytabersonine;16-Hydroxytabersonine;22149-28-6;Tabersonine, 11-hydroxy-;GV2G76UPD2;UNII-GV2G76UPD2;CHEBI:17699;methyl (1R,12R,19S)-12-ethyl-5-hydroxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate;1H-Indolizino(8,1-cd)carbazole, aspidospermidine-3-carboxylic acid deriv.;methyl 16-hydroxy-2,3,6,7-tetradehydro-5alpha,12beta,19alpha-aspidospermidine-3-carboxylate;Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-16-hydroxy-, methyl ester, (5alpha,12R,19alpha)-;SCHEMBL4131340;CHEMBL2011510;DTXSID601032123;HY-N1021;NSC815331;AKOS032962286;NSC-815331;CS-0016257;Q20179989;Methyl (5,12,19)-16-hydroxy-2,3,6,7-tetradehydroaspidospermidi ne-3-carboxylate;ASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 2,3,6,7-TETRADEHYDRO-16-HYDROXY-, METHYL ESTER, (5.ALPHA.,12R,19.ALPHA.)-

Suppliers and Price of 16-Hydroxytabersonine

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Crysdot
11-Hydroxytabersonine 95+%
5mg
$ 990.00

Arctom
11-Hydroxytabersonine
5mg
$ 643.00

Total 14 raw suppliers

Chemical Property of 16-Hydroxytabersonine

Chemical Property:

PSA：61.80000
LogP:3.00270
XLogP3:3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:352.17869263
Heavy Atom Count:26
Complexity:701

Purity/Quality:

99.5% ^*data from raw suppliers

11-Hydroxytabersonine 95+% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCC12CC(=C3C4(C1N(CC4)CC=C2)C5=C(N3)C=C(C=C5)O)C(=O)OC
Isomeric SMILES:CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)C5=C(N3)C=C(C=C5)O)C(=O)OC

Technology Process of 16-Hydroxytabersonine

There total 22 articles about 16-Hydroxytabersonine 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: 64.0%

: 29479-00-3
(-)-tabersonine hydrochloride

: 22149-28-6
11-hydroxytabersonine

Guidance literature:: With D-Galactose; water; In dimethyl sulfoxide; at 30 ℃; for 96h; Reagent/catalyst; Microbiological reaction; Enzymatic reaction;
DOI:10.1021/acs.jnatprod.0c00310

Reference yield:

: 287980-14-7
(-)-11-Mesyloxytabersonine

: 22149-28-6
11-hydroxytabersonine

Guidance literature:: With potassium hydroxide; In methanol; at 80 ℃; for 0.75h;

Reference yield:

: 20455-07-6
p-nitrophenyl methanesulfonate

: 22149-28-6
11-hydroxytabersonine

Guidance literature:: Multi-step reaction with 21 steps

1.1: H₂ / 10 percent Pd/C / methanol / 1 h / 20 °C

2.1: 0.33 h / 70 °C

3.1: HNO₃ / 0.5 h / 0 °C

4.1: HCl / methanol / 2 h / 70 °C

5.1: NaNO₂; aq. HCl / ethyl acetate / -15 °C

5.2: KI / ethyl acetate / 0.25 h / -15 °C

6.1: 83 percent / BnEt₃NCl / Pd(OAc)2 / dimethylformamide / 2 h / 50 °C

7.1: NaBH₄ / methanol / 0.5 h / -15 °C

8.1: pyridine / 0.25 h / 20 °C

9.1: Zn; AcOH / CH₂Cl₂ / 0.5 h / 20 °C

10.1: Ac₂O / CH₂Cl₂ / 0.5 h / 0 °C

11.1: 89 percent / POCl₃; pyridine / CH₂Cl₂ / 0.67 h / 0 °C

12.1: n-Bu₃SnH; AIBN / acetonitrile / 0.5 h / 80 °C

12.2: I₂ / acetonitrile / 0.33 h / 20 °C

13.1: Et₃N; DMAP / acetonitrile / 1 h / 20 °C

14.1: Ph₃As; CuI / BnPd(PPh₃)2Cl / hexamethylphosphoric acid triamide; dimethylformamide / 3.5 h / 85 °C

15.1: Na₂CO₃; H₂O / methanol / 2 h / 20 °C

16.1: 89 percent / diethyl azodicarboxylate; PPh₃ / benzene; toluene / 0.5 h / 20 °C

17.1: TFA / CH₂Cl₂ / 0.25 h / 20 °C

18.1: pyrrolidine / methanol; acetonitrile / 0.08 h / 20 °C

19.1: pyrrolidine / methanol; acetonitrile / 4 h / Heating

20.1: 88 percent / PPh₃ / CCl₄; acetonitrile / 0.5 h / 70 °C

21.1: KOH / methanol / 0.75 h / 80 °C

With pyrrolidine; pyridine; hydrogenchloride; dmap; potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; 2,2'-azobis(isobutyronitrile); triphenyl-arsane; N-benzyl-N,N,N-triethylammonium chloride; water; hydrogen; nitric acid; tri-n-butyl-tin hydride; acetic anhydride; sodium carbonate; acetic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; zinc; sodium nitrite; diethylazodicarboxylate; trichlorophosphate; palladium diacetate; palladium on activated charcoal; trans benzyl(chloro)bis(triphenylphosphine)palladium(II); In methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 1.1: Catalytic hydrogenation / 2.1: Acetylation / 3.1: Nitration / 4.1: Deacetylation / 5.1: Diazotization / 5.2: Iodination / 6.1: phosphine-free Heck reaction / 7.1: Reduction / 8.1: Acetylation / 9.1: Reduction / 10.1: Formylation / 11.1: Dehydration / 12.1: Cyclization / 12.2: Iodination / 13.1: Acylation / 14.1: Alkylation / 15.1: Hydrolysis / 16.1: Alkylation / 17.1: deacylation; hydration / 18.1: sulfonamide cleavage / 19.1: Cyclization / 20.1: Dehydration / 21.1: Hydrolysis;