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

Base Information

• Chemical Name: (S)-Pyrrolidine-1,2-dicarboxylic acid 2-{(1S,3S,5S,6S)-5-acetoxy-1-tert-butyl-3-methyl-6-[(E)-(S)-3-(3-methyl-but-2-enyloxycarbonyl)-1-tritylsulfanylmethyl-but-2-enylcarbamoyl]-heptyl} ester 1-(9H-fluoren-9-ylmethyl) ester
• CAS No.: 1026851-31-9
• Molecular Formula: C₆₅H₇₆N₂O₉S
• Molecular Weight: 1061.39
• Mol file: 1026851-31-9.mol

Synonyms:

Chemical Property of (S)-Pyrrolidine-1,2-dicarboxylic acid 2-{(1S,3S,5S,6S)-5-acetoxy-1-tert-butyl-3-methyl-6-[(E)-(S)-3-(3-methyl-but-2-enyloxycarbonyl)-1-tritylsulfanylmethyl-but-2-enylcarbamoyl]-heptyl} ester 1-(9H-fluoren-9-ylmethyl) 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)-5-acetoxy-1-tert-butyl-3-methyl-6-[(E)-(S)-3-(3-methyl-but-2-enyloxycarbonyl)-1-tritylsulfanylmethyl-but-2-enylcarbamoyl]-heptyl} ester 1-(9H-fluoren-9-ylmethyl) ester

There total 29 articles about (S)-Pyrrolidine-1,2-dicarboxylic acid 2-{(1S,3S,5S,6S)-5-acetoxy-1-tert-butyl-3-methyl-6-[(E)-(S)-3-(3-methyl-but-2-enyloxycarbonyl)-1-tritylsulfanylmethyl-but-2-enylcarbamoyl]-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:

(3S)-2,2-dimethyl-5-hexen-3-ol (67760-86-5) → (S)-Pyrrolidine-1,2-dicarboxylic acid 2-{(1S,3S,5S,6S)-5-acetoxy-1-tert-butyl-3-methyl-6-[(E)-(S)-3-(3-methyl-but-2-enyloxycarbonyl)-1-tritylsulfanylmethyl-but-2-enylcarbamoyl]-heptyl} ester 1-(9H-fluoren-9-ylmethyl) ester (1026851-31-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 90 percent / Et₃N

2.1: 80 percent / Grubbs' first generation catalyst

3.1: 94 percent / CuCN / diethyl ether; diethyl ether / 1 h

4.1: LiAlH₄ / tetrahydrofuran / 1 h / Heating

5.1: pyridine / CH₂Cl₂

6.1: K₂CO₃ / methanol; H₂O / 5 h

7.1: 2.3 g / Dess-Martin reagent / CH₂Cl₂ / 3 h

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

8.2: 90 percent / TiCl₄ / hexane; CH₂Cl₂ / 2 h

9.1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

10.1: 1.05 g / PPTs / 24 h

11.1: 90 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene

12.1: TsOH / methanol

13.1: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h

14.1: 155 mg / NaClO₂; NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 1 h

15.1: 237 mg / HATU; DIPEA / CH₂Cl₂ / 12 h / 20 °C

16.1: 81 percent / DIPEA / CH₂Cl₂ / 1.5 h

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; triethyl borane; trifluorormethanesulfonic acid; 2,4,6-trichlorobenzoyl chloride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 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; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 7.1: Dess-Martin oxidation;

DOI:10.1002/chem.200600599

Reference yield:

(S)-5,5-dimethyl-4-hydroxyhexan-2-one (197454-20-9) → (S)-Pyrrolidine-1,2-dicarboxylic acid 2-{(1S,3S,5S,6S)-5-acetoxy-1-tert-butyl-3-methyl-6-[(E)-(S)-3-(3-methyl-but-2-enyloxycarbonyl)-1-tritylsulfanylmethyl-but-2-enylcarbamoyl]-heptyl} ester 1-(9H-fluoren-9-ylmethyl) ester (1026851-31-9)

Guidance literature:

Multi-step reaction with 22 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: 237 mg / HATU; DIPEA / CH₂Cl₂ / 12 h / 20 °C

22.1: 81 percent / DIPEA / CH₂Cl₂ / 1.5 h

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:

(4R,6S)-6-tert-butyl-4-methyltetrahydro-2H-pyran-2-one (531559-40-7) → (S)-Pyrrolidine-1,2-dicarboxylic acid 2-{(1S,3S,5S,6S)-5-acetoxy-1-tert-butyl-3-methyl-6-[(E)-(S)-3-(3-methyl-but-2-enyloxycarbonyl)-1-tritylsulfanylmethyl-but-2-enylcarbamoyl]-heptyl} ester 1-(9H-fluoren-9-ylmethyl) ester (1026851-31-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: LiAlH₄ / tetrahydrofuran / 1 h / Heating

2.1: pyridine / CH₂Cl₂

3.1: K₂CO₃ / methanol; H₂O / 5 h

4.1: 2.3 g / Dess-Martin reagent / CH₂Cl₂ / 3 h

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

5.2: 90 percent / TiCl₄ / hexane; CH₂Cl₂ / 2 h

6.1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

7.1: 1.05 g / PPTs / 24 h

8.1: 90 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene

9.1: TsOH / methanol

10.1: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h

11.1: 155 mg / NaClO₂; NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 1 h

12.1: 237 mg / HATU; DIPEA / CH₂Cl₂ / 12 h / 20 °C

13.1: 81 percent / DIPEA / CH₂Cl₂ / 1.5 h

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; triethyl borane; trifluorormethanesulfonic acid; 2,4,6-trichlorobenzoyl chloride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 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; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 4.1: Dess-Martin oxidation;

DOI:10.1002/chem.200600599

upstream raw materials:

[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 3-methyl-but-2-enyl ester

(3S)-2,2-dimethyl-5-hexen-3-ol

(S)-5,5-dimethyl-4-hydroxyhexan-2-one

Downstream raw materials:

(-)-apratoxin A

C₆₇H₉₅N₅O₁₂SSi