Kazusamycin A

Base Information

Chemical Name:Kazusamycin A
CAS No.:92090-94-3
Deprecated CAS:94664-05-8
Molecular Formula:C₃₃H₄₈O₇
Molecular Weight:556.74
Hs Code.:
UNII:9F2Y3169IP
ChEMBL ID:CHEMBL207141
DSSTox Substance ID:DTXSID801098454
Nikkaji Number:J22.915F
Wikidata:Q27896151
Mol file:92090-94-3.mol

Synonyms:16-hydroxyleptomycin B;hydroxyelactocin;kazusamycin;kazusamycin A;PD 114,721;PD-114721

Suppliers and Price of Kazusamycin A

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

Usbiological
Kazusamycin A
100ug
$ 619.00

TRC
KazusamycinA
100μg
$ 400.00

TRC
KazusamycinA
250μg
$ 805.00

Cayman Chemical
Kazusamycin A ≥95%
500μg
$ 956.00

Cayman Chemical
Kazusamycin A ≥95%
100μg
$ 425.00

American Custom Chemicals Corporation
KAZUSAMYCIN A 95.00%
5MG
$ 497.72

Total 5 raw suppliers

Chemical Property of Kazusamycin A

Chemical Property:

Vapor Pressure:9.14E-27mmHg at 25°C
Boiling Point:761.5°Cat760mmHg
Flash Point:236.7°C
PSA：121.13000
Density:1.109g/cm³
LogP:5.75710
Storage Temp.:−20°C
Solubility.:methanol/water: 7:3, soluble
XLogP3:6.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:16
Exact Mass:556.34000387
Heavy Atom Count:40
Complexity:1040

Purity/Quality:

95%（70% Methanol solution） ^*data from raw suppliers

Kazusamycin A ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:F,T
Statements: 11-23/24/25-39/23/24/25
Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Canonical SMILES:CCC(=CC(C)CC=CC(=CC(CO)C(=O)C(C)C(C(C)CC(=CC(=O)O)C)O)C)C=CC1C(C=CC(=O)O1)C
Isomeric SMILES:CC/C(=C/[C@H](C)C/C=C/C(=C/[C@@H](CO)C(=O)[C@@H](C)[C@@H]([C@@H](C)C/C(=C/C(=O)O)/C)O)/C)/C=C/[C@H]1[C@H](C=CC(=O)O1)C
Uses Kazusamycin A is a minor member of the leptomycin complex isolated from some Streptomyces species. It is an hydroxylated analogue of leptomycin B, a nuclear export inhibitor. Kazusamycin A exhibits potent antitumour activity both in vitro and in vivo against P388 and L1210 cell lines, and also shows strong antibacterial and antifungal activity. Kazusamycin A is a potent antibiotic shown to induce G2 cell cycle arrest and delay M phase.

Technology Process of Kazusamycin A

There total 40 articles about Kazusamycin A 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: 74.0%

: 753016-62-5
(2E,10E,12E,16Z,18E)-(5S,6R,7S,9S,15R)-6-(tert-Butyl-dimethyl-silanyloxy)-17-ethyl-3,5,7,11,15-pentamethyl-19-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxo-9-triisopropylsilanyloxymethyl-nonadeca-2,10,12,16,18-pentaenoic acid

: 92090-94-3,94664-05-8
(-)-kazusamycin A

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 96h;
DOI:10.1021/ol049219z

Reference yield:

: 71565-21-4
(2S,4'R)-(+)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-propanol

: 92090-94-3,94664-05-8
(-)-kazusamycin A

Guidance literature:: Multi-step reaction with 21 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

2.1: PPh₃; Zn powder / CH₂Cl₂ / 24 h / 20 °C

2.2: 440.7 mg / CH₂Cl₂ / 2 h / 20 °C

3.1: BuLi / tetrahydrofuran; hexane / -78 - 20 °C

3.2: 93 percent / tetrahydrofuran / -78 - 20 °C

4.1: 96 percent / H₂ / Lindlar catalyst / methanol / 20 h / 20 °C

5.1: Dowex 50W X₈ / methanol / 7 h / 20 °C

5.2: Amberlyst 15 / CH₂Cl₂ / 12 h / 20 °C

5.3: 57 percent / imidazole / dimethylformamide / 4 h / 20 °C

6.1: 82 percent / DIBAL / CH₂Cl₂ / -78 °C

7.1: 85 percent / PPTS / benzene

8.1: 85 percent / TBAF / tetrahydrofuran

9.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

9.2: 98 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

10.1: Bu₃P / acetonitrile / 0.75 h / 20 °C

10.2: 91 percent / tBuOK / toluene; tetrahydrofuran / 0.75 h / 0 °C

11.1: 99 percent / TBAF / tetrahydrofuran / 6.5 h / 20 °C

12.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.42 h / -78 °C

12.2: 92 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

13.1: Bu₃P / acetonitrile / 1 h / 20 °C

13.2: tBuOK / toluene; tetrahydrofuran / 1 h / 0 °C

14.1: PPTS / methanol / 20 h / 20 °C

15.1: imidazole / dimethylformamide / 3 h

16.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.67 h / 20 °C

17.1: PPTS / acetone; H₂O / 28 h / 20 °C

18.1: dimedone / Pd(PPh₃)4 / tetrahydrofuran / 1.5 h / 20 °C

19.1: 49 percent / pyridine; MnO₂ / CH₂Cl₂ / 1 h / 20 °C

20.1: 80 percent / NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol / 2 h / 20 °C

21.1: 74 percent / pyridine; HF*pyridine / tetrahydrofuran / 96 h / 20 °C

With pyridine; 1H-imidazole; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; tributylphosphine; Dowex 50W X₈; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimedone; pyridine hydrogenfluoride; dimethyl sulfoxide; triphenylphosphine; zinc; Lindlar's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 10.2: Wittig olefination / 13.2: Wittig reaction;
DOI:10.1021/ol049219z

Reference yield:

: 77398-87-9
(2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanal

: 92090-94-3,94664-05-8
(-)-kazusamycin A

Guidance literature:: Multi-step reaction with 20 steps

1.1: PPh₃; Zn powder / CH₂Cl₂ / 24 h / 20 °C

1.2: 440.7 mg / CH₂Cl₂ / 2 h / 20 °C

2.1: BuLi / tetrahydrofuran; hexane / -78 - 20 °C

2.2: 93 percent / tetrahydrofuran / -78 - 20 °C

3.1: 96 percent / H₂ / Lindlar catalyst / methanol / 20 h / 20 °C

4.1: Dowex 50W X₈ / methanol / 7 h / 20 °C

4.2: Amberlyst 15 / CH₂Cl₂ / 12 h / 20 °C

4.3: 57 percent / imidazole / dimethylformamide / 4 h / 20 °C

5.1: 82 percent / DIBAL / CH₂Cl₂ / -78 °C

6.1: 85 percent / PPTS / benzene

7.1: 85 percent / TBAF / tetrahydrofuran

8.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

8.2: 98 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

9.1: Bu₃P / acetonitrile / 0.75 h / 20 °C

9.2: 91 percent / tBuOK / toluene; tetrahydrofuran / 0.75 h / 0 °C

10.1: 99 percent / TBAF / tetrahydrofuran / 6.5 h / 20 °C

11.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.42 h / -78 °C

11.2: 92 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

12.1: Bu₃P / acetonitrile / 1 h / 20 °C

12.2: tBuOK / toluene; tetrahydrofuran / 1 h / 0 °C

13.1: PPTS / methanol / 20 h / 20 °C

14.1: imidazole / dimethylformamide / 3 h

15.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.67 h / 20 °C

16.1: PPTS / acetone; H₂O / 28 h / 20 °C

17.1: dimedone / Pd(PPh₃)4 / tetrahydrofuran / 1.5 h / 20 °C

18.1: 49 percent / pyridine; MnO₂ / CH₂Cl₂ / 1 h / 20 °C

19.1: 80 percent / NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol / 2 h / 20 °C

20.1: 74 percent / pyridine; HF*pyridine / tetrahydrofuran / 96 h / 20 °C

With pyridine; 1H-imidazole; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; tributylphosphine; Dowex 50W X₈; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimedone; pyridine hydrogenfluoride; dimethyl sulfoxide; triphenylphosphine; zinc; Lindlar's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 9.2: Wittig olefination / 12.2: Wittig reaction;
DOI:10.1021/ol049219z