(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

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-(9H-fluoren-9-ylmethyl) ester
• CAS No.: 878626-89-2
• Molecular Formula: C₆₁H₇₀N₂O₈S
• Molecular Weight: 991.301

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-(9H-fluoren-9-ylmethyl) 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-(9H-fluoren-9-ylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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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-(9H-fluoren-9-ylmethyl) ester

There total 52 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-(9H-fluoren-9-ylmethyl) 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:

(S)-5,5-dimethyl-4-hydroxyhexan-2-one (197454-20-9) → (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 (878626-89-2)

Guidance literature:

Multi-step reaction with 21 steps

1.1: 15 g / imidazole / dimethylformamide / 24 h

2.1: NaBH₄ / methanol / 0.5 h

3.1: Et₃N / CH₂Cl₂ / 2 h / 0 °C

4.1: 10 g / tBuOK / toluene / 1 h / Heating

5.1: ozone / CH₂Cl₂ / -78 - 20 °C

5.2: Me₂S / CH₂Cl₂ / 24 h / 40 °C

6.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.33 h / -78 °C

6.2: hexane; tetrahydrofuran / 1 h

7.1: aq. HF / acetonitrile / 20 °C

8.1: 1.75 g / Et₃N; MsCl / CH₂Cl₂ / 2 h

9.1: 94 percent / CuCN / diethyl ether; diethyl ether / 1 h

10.1: LiAlH₄ / tetrahydrofuran / 1 h / Heating

11.1: pyridine / CH₂Cl₂

12.1: K₂CO₃ / methanol; H₂O / 5 h

13.1: 2.3 g / Dess-Martin reagent / CH₂Cl₂ / 3 h

14.1: CF₃SO₃H; Et₃B; DIPEA / hexane; CH₂Cl₂ / 0.5 h / -10 °C

14.2: 90 percent / TiCl₄ / hexane; CH₂Cl₂ / 2 h

15.1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

16.1: 1.05 g / PPTs / 24 h

17.1: 90 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene

18.1: TsOH / methanol

19.1: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h

20.1: 155 mg / NaClO₂; NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 1 h

21.1: HATU; iPr₂NEt

With pyridine; 1H-imidazole; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; triethyl borane; trifluorormethanesulfonic acid; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; potassium tert-butylate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; methanesulfonyl chloride; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; sodium hypochlorite; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene; 13.1: Dess-Martin oxidation;

DOI:10.1002/chem.200600599

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-(9H-fluoren-9-ylmethyl) ester (878626-89-2)

Guidance literature:

Multi-step reaction with 16 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

15.1: 2,6-lutidine; TMDOTf / CH₂Cl₂ / 0.5 h / 20 °C

16.1: 359 mg / iPr₂NEt / CH₂Cl₂; tetrahydrofuran / 0.67 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium periodate; oxalyl dichloride; N,N-dimethyl-ethanamine; TMDOTf; 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-(9H-fluoren-9-ylmethyl) ester (878626-89-2)

Guidance literature:

Multi-step reaction with 15 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

14.1: 2,6-lutidine; TMDOTf / CH₂Cl₂ / 0.5 h / 20 °C

15.1: 359 mg / iPr₂NEt / CH₂Cl₂; tetrahydrofuran / 0.67 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium periodate; oxalyl dichloride; N,N-dimethyl-ethanamine; TMDOTf; 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:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(S)-Pyrrolidine-1,2-dicarboxylic acid 2-((1S,3S,5S,6S)-1-tert-butyl-6-carboxy-5-hydroxy-3-methyl-heptyl) ester 1-(9H-fluoren-9-ylmethyl) ester

[1-(methoxy-methyl-carbamoyl)-2-tritylsulfanyl-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

(E)-(S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-5-tritylsulfanyl-pent-2-enoic acid allyl ester

Downstream raw materials:

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

pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl ester

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

(-)-apratoxin A

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