kazusamycin A

Base Information

• Chemical Name: kazusamycin A
• CAS No.: 94664-05-8
• Molecular Formula: C₃₃H₄₈O₇
• Molecular Weight: 556.74
• Mol file: 94664-05-8.mol

Synonyms:(2E,5S,6R,7S,9S,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-9-(hydroxymethyl)-3,5,7,11,15-pentamethyl-19-[(2S,3S)-3-methyl-6-oxo-2,3-dihydropyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid

Chemical Property of kazusamycin A

Chemical Property:

• Vapor Pressure: 9.14E-27mmHg at 25°C
• Boiling Point: 761.5°C at 760 mmHg
• Flash Point: 236.7°C
• Density: 1.109g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(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 (753016-62-5) → (-)-kazusamycin A (92090-94-3,94664-05-8)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 96h;

DOI:10.1021/ol049219z

Reference yield:

(2S,4'R)-(+)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-propanol (71565-21-4) → (-)-kazusamycin A (92090-94-3,94664-05-8)

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:

(2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanal (77398-87-9) → (-)-kazusamycin A (92090-94-3,94664-05-8)

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

upstream raw materials:

(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

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

(2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanal

(R)-4-((S)-3,3-Dibromo-1-methyl-allyl)-2,2-dimethyl-[1,3]dioxolane

Refernces