C₆₇H₉₅N₅O₁₂SSi

Base Information

• Chemical Name: C₆₇H₉₅N₅O₁₂SSi
• CAS No.: 916912-49-7
• Molecular Formula: C₆₇H₉₅N₅O₁₂SSi
• Molecular Weight: 1222.67
• Mol file: 916912-49-7.mol

Synonyms:

Chemical Property of C₆₇H₉₅N₅O₁₂SSi

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₆₇H₉₅N₅O₁₂SSi

There total 35 articles about C₆₇H₉₅N₅O₁₂SSi 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) → C67H95N5O12SSi (916912-49-7)

Guidance literature:

Multi-step reaction with 19 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

17.1: 92 percent / trifluoromethanesulfonic anhydride; triphenylphosphine oxide / CH₂Cl₂ / 1 h / 0 °C

18.1: TMSOTf / CH₂Cl₂ / 1 h

19.1: 38 mg / HATU; DIPEA / CH₂Cl₂ / 20 °C

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; triethyl borane; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; trifluoromethanesulfonic acid anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; Triphenylphosphine oxide; 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) → C67H95N5O12SSi (916912-49-7)

Guidance literature:

Multi-step reaction with 25 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

23.1: 92 percent / trifluoromethanesulfonic anhydride; triphenylphosphine oxide / CH₂Cl₂ / 1 h / 0 °C

24.1: TMSOTf / CH₂Cl₂ / 1 h

25.1: 38 mg / HATU; DIPEA / CH₂Cl₂ / 20 °C

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; trimethylsilyl trifluoromethanesulfonate; 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; trifluoromethanesulfonic acid anhydride; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; Triphenylphosphine oxide; 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:

N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine (77128-72-4,201335-88-8) → C67H95N5O12SSi (916912-49-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 2-bromo-1-ethyl-pyridinium tetrafluoroborate; DIPEA / CH₂Cl₂ / 24 h / 0 °C

2: H₂ / Pd/C / ethyl acetate / 12 h / 20 °C / 760 Torr

3: 90 mg / 2-bromo-1-ethyl-pyridinium tetrafluoroborate; DIPEA / CH₂Cl₂ / 24 h / 0 °C

4: Et₂NH / acetonitrile / 0.25 h

5: 38 mg / HATU; DIPEA / CH₂Cl₂ / 20 °C

With hydrogen; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; diethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1002/chem.200600599

upstream raw materials:

(E)-(S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-5-tritylsulfanyl-pent-2-enoic acid 3-methyl-but-2-enyl ester

(S)-Pyrrolidine-1,2-dicarboxylic acid 2-((1S,3S,5S,6S)-5-acetoxy-1-tert-butyl-3-methyl-6-{(S)-4-[(E)-2-(3-methyl-but-2-enyloxycarbonyl)-propenyl]-4,5-dihydro-thiazol-2-yl}-heptyl) ester 1-(9H-fluoren-9-ylmethyl) ester

(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

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

Downstream raw materials:

(-)-apratoxin A

Refernces