Fostriecin

Base Information

Chemical Name:Fostriecin
CAS No.:87810-56-8
Molecular Formula:C₁₉H₂₇O₉P
Molecular Weight:430.392
Hs Code.:
UNII:ZO1648L551
DSSTox Substance ID:DTXSID00868985
Nikkaji Number:J22.037J
Wikipedia:Fostriecin
Wikidata:Q27295794
NCI Thesaurus Code:C1372
Metabolomics Workbench ID:144244
Mol file:87810-56-8.mol

Synonyms:CI 920;CI-920;fostriecin;PD 110161;PD-110,161

Suppliers and Price of Fostriecin

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

American Custom Chemicals Corporation
FOSTRIECIN 98.00%
50MG
$ 1224.30

Total 5 raw suppliers

Chemical Property of Fostriecin

Chemical Property:

Vapor Pressure:3.93E-25mmHg at 25°C
Melting Point:77oC
Boiling Point:737.9°C at 760 mmHg
Flash Point:400.1°C
PSA：163.56000
Density:1.413g/cm³
LogP:1.05510
XLogP3:-0.5
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:11
Exact Mass:430.13926943
Heavy Atom Count:29
Complexity:719

Purity/Quality:

>95% by HPLC ^*data from raw suppliers

FOSTRIECIN 98.00% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C=CC1CC=CC(=O)O1)(C(CC(C=CC=CC=CCO)O)OP(=O)(O)O)O
Isomeric SMILES:C[C@@](/C=C/[C@H]1CC=CC(=O)O1)([C@@H](C[C@H](/C=C\C=C/C=C/CO)O)OP(=O)(O)O)O
Uses Fostriecin is the most fully characterised member of a family of phosphate esters of a triene antibiotic. The antitumour potential of fostriecin has attracted considerable interest, focused on its mode of action as a topoisomerase II inhibitor. Subsequent research has focused on this metabolite's selective inhibition of protein phosphatase PP2A.

Technology Process of Fostriecin

There total 81 articles about Fostriecin 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: 79.0%

: 381665-55-0
Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl} ester

: 87810-56-8
(+)-fostriecin

Guidance literature:: With pyridine; hydrogen fluoride; In acetonitrile;
DOI:10.1039/b209742g

Reference yield: 38.0%

: 575456-24-5
Phosphoric acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester

: 87810-56-8
(+)-fostriecin

Guidance literature:: Phosphoric acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester; With hydrogen fluoride; In acetonitrile;

With pyridine; at 20 ℃; for 20h; Further stages.;
DOI:10.1039/b201302a

Reference yield:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 87810-56-8
(+)-fostriecin

Guidance literature:: Multi-step reaction with 28 steps

1.1: 95 percent / BF₃*OEt₂ / cyclohexane; CH₂Cl₂ / 25 °C

2.1: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

3.1: 73 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 2.5 h / Heating

4.1: (DHQD)2AQN; K₂OsO₂(OH)4; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 24 h / 2 °C

5.1: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C

7.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

8.1: 90 percent / DIBAL-H / toluene; hexane / 0.33 h / -20 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

10.1: PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

10.2: 3.90 g / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

11.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 25 °C

12.1: 93 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 0.5 h / 25 °C

13.1: 84 percent / Bu₃SnH; (Ph₃P)4Pd / benzene / 2.5 h / 25 °C

14.1: 83 percent / iPr₂NEt; 1-methyl-2-pyrrolidinone; (CH₃CN)2PdCl₂ / 2 h / 25 °C

15.1: 98 percent / DIBAL-H / toluene / 0.08 h / -78 °C

16.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

17.1: BuLi / toluene; hexane / 0.25 h / -78 °C

17.2: toluene; hexane / 0.25 h / -78 °C

18.1: 140 mg / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

19.1: 75 percent / t-BuOK / toluene; tetrahydrofuran / 2 h / 0 °C

20.1: CeCl₃; t-BuLi / tetrahydrofuran; diethyl ether / 0.17 h / -78 °C

20.2: tetrahydrofuran; diethyl ether; toluene / 0.08 h / -78 °C

21.1: PPTS / 2 h / 25 °C

22.1: Et₃N / DMAP / CH₂Cl₂ / 1 h

23.1: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -20 °C

24.1: aq. HCl / acetone / 2 h / -15 - 0 °C

25.1: 40 percent / Ag₂CO₃-Celite / benzene / 2 h / 80 °C

26.1: PCl₃; pyridine / 0.25 h / 25 °C

26.2: 1 h

27.1: 3.9 mg / aq. H₂O₂ / CH₂Cl₂; pyridine / 0.5 h

28.1: aq. HF / acetonitrile / 0.25 h / 25 °C

28.2: aq. HF; pyridine / acetonitrile / 168000 h

With pyridine; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; hydrogenchloride; dmap; dichloro bis(acetonitrile) palladium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; cerium(III) chloride; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; dihydrogen peroxide; tert.-butyl lithium; tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; silver carbonate; acetonitrile; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); phosphorus trichloride; dmap; methanesulfonamide; pyridinium p-toluenesulfonate; potassium carbonate; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; cyclohexane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene; 4.1: Sharpless assymetric dihydroxylation / 9.1: Dess-Martin oxidation / 10.1: Corey and Fuchs reaction / 14.1: Stille coupling / 15.1: Stille coupling / 16.1: Dess-Martin oxidation / 18.1: Dess-Martin oxidation;
DOI:10.1021/ja010195q