apratoxin S₅

Base Information

• Chemical Name: apratoxin S₅
• CAS No.: 1334149-95-9
• Molecular Formula: C₄₄H₆₉N₅O₈S
• Molecular Weight: 828.127
• Mol file: 1334149-95-9.mol

Synonyms:apratoxin S₅

Chemical Property of apratoxin S₅

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of apratoxin S₅

There total 15 articles about apratoxin S₅ 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:

C44H71N5O9S → apratoxin S5 (1334149-95-9) + apratoxin S4 (1334149-94-8) + apratoxin S6 (1334149-96-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 0 - 20 ℃; for 20.5h;

DOI:10.1021/ml200176m

Reference yield:

C18H28O4 → apratoxin S5 (1334149-95-9) + apratoxin S4 (1334149-94-8) + apratoxin S6 (1334149-96-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: toluene / 6.25 h / -78 °C / Molecular sieve

1.2: 0.5 h / 0 °C

2.1: pyridine; dmap / dichloromethane / 1 h / 0 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 0 °C

4.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / toluene / 0.17 h / 20 °C / Inert atmosphere

4.2: 4 h / 20 °C / Inert atmosphere

5.1: osmium(VIII) oxide; sodium hydrogencarbonate / N,N-dimethyl-formamide; tert-butyl alcohol / 15 h / 20 °C

5.2: 5 h / 20 °C

6.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 °C

7.1: trifluoromethylsulfonic anhydride; Triphenylphosphine oxide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.1: ammonium acetate; zinc / tetrahydrofuran; water / 0.5 h / 20 °C

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methylaniline / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Darkness

10.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 10 h / 20 °C

11.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methylaniline / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Darkness

12.1: diethylamine / acetonitrile

13.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20.5 h / 0 - 20 °C

With pyridine; dmap; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; trifluoromethylsulfonic anhydride; 2,4,6-trichlorobenzoyl chloride; ammonium acetate; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; N-ethyl-N,N-diisopropylamine; HATU; N-methylaniline; Triphenylphosphine oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ml200176m

Reference yield:

(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate (1177263-65-8) → apratoxin S5 (1334149-95-9) + apratoxin S4 (1334149-94-8) + apratoxin S6 (1334149-96-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 0 °C

2.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / toluene / 0.17 h / 20 °C / Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere

3.1: osmium(VIII) oxide; sodium hydrogencarbonate / N,N-dimethyl-formamide; tert-butyl alcohol / 15 h / 20 °C

3.2: 5 h / 20 °C

4.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 °C

5.1: trifluoromethylsulfonic anhydride; Triphenylphosphine oxide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

6.1: ammonium acetate; zinc / tetrahydrofuran; water / 0.5 h / 20 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methylaniline / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Darkness

8.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 10 h / 20 °C

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methylaniline / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Darkness

10.1: diethylamine / acetonitrile

11.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20.5 h / 0 - 20 °C

With osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; trifluoromethylsulfonic anhydride; 2,4,6-trichlorobenzoyl chloride; ammonium acetate; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; N-ethyl-N,N-diisopropylamine; HATU; N-methylaniline; Triphenylphosphine oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ml200176m

upstream raw materials:

(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate

pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(3R,4S,6S,8S)-8-tert-butyl-4-(2,2,2-trichloroethoxycarbonyloxy)-3,6-dimethyloct-1-en-8-yl]ester 1-(9H-fluoren-9-ylmethyl)ester

pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S)-1-tert-butyl-6-carboxy-5-(2,2,2-trichloroethoxycarbonyloxy)-3-methylhept-1-yl]ester 1-(9H-fluoren-9-ylmethyl)ester

(4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester

Downstream raw materials:

N-methylalanine

N-methyl-L-isoleucine

O-Methyltyrosine

D-Prolin