(S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-tert-butyl ester

Base Information

• Chemical Name: (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-tert-butyl ester
• CAS No.: 878626-88-1
• Molecular Formula: C₅₁H₆₈N₂O₈S
• Molecular Weight: 869.176
• Mol file: 878626-88-1.mol

Synonyms:(S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-tert-butyl ester

Chemical Property of (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-tert-butyl ester

There total 23 articles about (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-tert-butyl ester 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: 95.0%

(S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3R,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-heptyl] ester 1-tert-butyl ester (878626-80-3) → (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-tert-butyl ester (878626-88-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.333333h;

DOI:10.1021/ol052907d

Reference yield:

(S)-5,5-dimethyl-4-(4-methoxybenzyloxy)-2-hexanone (878626-87-0) → (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-tert-butyl ester (878626-88-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: tetrahydrofuran / 0.5 h / 0 °C

2.1: pyridine; DMAP / 24 h / 50 °C

3.1: PdCl₂(CH₃CN)2 / tetrahydrofuran / 2 h / 20 °C

4.1: 3.29 g / K₂CO₃ / methanol / 1.5 h / 0 °C

5.1: 100 percent / H₂ / Ru(OAc)2[(S)-binap] / methanol / 24 h / 50 °C

6.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

7.1: (c-hex)2BCl; Me₂NEt / diethyl ether / 15 h / -78 - -20 °C

8.1: 894 mg / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9.1: DDQ / CH₂Cl₂; H₂O / 0.5 h / 0 °C / pH 7

10.1: iPr₂NEt; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 10 h / 20 °C

10.2: 78 percent / DMAP / toluene / 3 h / 20 °C

11.1: K₂CO₃ / methanol / 1.5 h / 20 °C

12.1: 445 mg / NaIO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

13.1: 372 mg / iPr₂NEt; HATU / CH₂Cl₂ / 10 h / 20 °C

14.1: 95 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium periodate; oxalyl dichloride; N,N-dimethyl-ethanamine; 2,4,6-trichlorobenzoyl chloride; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; dichloro bis(acetonitrile) palladium(II); Ru(OCOCH₃)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 6.1: Swern oxidation / 7.1: aldol reaction;

DOI:10.1021/ol052907d

Reference yield:

(S)-5-(4-Methoxy-benzyloxy)-3,6,6-trimethyl-hept-1-en-3-ol → (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-tert-butyl ester (878626-88-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: pyridine; DMAP / 24 h / 50 °C

2.1: PdCl₂(CH₃CN)2 / tetrahydrofuran / 2 h / 20 °C

3.1: 3.29 g / K₂CO₃ / methanol / 1.5 h / 0 °C

4.1: 100 percent / H₂ / Ru(OAc)2[(S)-binap] / methanol / 24 h / 50 °C

5.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

6.1: (c-hex)2BCl; Me₂NEt / diethyl ether / 15 h / -78 - -20 °C

7.1: 894 mg / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

8.1: DDQ / CH₂Cl₂; H₂O / 0.5 h / 0 °C / pH 7

9.1: iPr₂NEt; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 10 h / 20 °C

9.2: 78 percent / DMAP / toluene / 3 h / 20 °C

10.1: K₂CO₃ / methanol / 1.5 h / 20 °C

11.1: 445 mg / NaIO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

12.1: 372 mg / iPr₂NEt; HATU / CH₂Cl₂ / 10 h / 20 °C

13.1: 95 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium periodate; oxalyl dichloride; N,N-dimethyl-ethanamine; 2,4,6-trichlorobenzoyl chloride; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; dichloro bis(acetonitrile) palladium(II); Ru(OCOCH₃)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 5.1: Swern oxidation / 6.1: aldol reaction;

DOI:10.1021/ol052907d

upstream raw materials:

(S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3R,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-heptyl] ester 1-tert-butyl ester

(S)-5,5-dimethyl-4-(4-methoxybenzyloxy)-2-hexanone

(E)-(S)-5-(4-methoxybenzyloxy)-3,6,6-trimethyl-2-hepten-1-ol

acetic acid 1-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-butyl]-1-methyl-allyl ester

Downstream raw materials:

(-)-apratoxin A

1-[(9H-fluoren-9-yl)methyl] 2-[(3S,5S,7S,8S)-8-({S}-4-{[5S,8S,11S,E]-11-[(S)-sec-butyl]-5-[4-methoxybenzyl]-2,7,8,10-tetramethyl-3,6,9,12-tetraoxo-13-oxa-4,7,10-triazahexadeca-1,15-dien-1-yl}-4,5-dihydrothiazol-2-yl)-7-hydroxy-2,2,5-trimethylnonan-3-yl] (S)-pyrrolidine-1,2-dicarboxylate

1-[(9H-fluoren-9-yl)methyl] 2-[(3S,5S,7S,8S)-9-{[(S,E)-5-(allyloxy)-4-methyl-5-oxo-1-(tritylthio)pent-3-en-2-yl]amino}-2,2,5,8-tetramethyl-9-oxo-7-{[(2,2,2-trichloroethoxy)carbonyl]oxy}nonan-3-yl] (S)-pyrrolidine-1,2-dicarboxylate

(S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-(9H-fluoren-9-ylmethyl) ester

Refernces