Acetic acid (1S,3S,5S,6S)-7-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-hydroxy-1-isopropyl-3,6-dimethyl-7-oxo-heptyl ester

Base Information

• Chemical Name: Acetic acid (1S,3S,5S,6S)-7-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-hydroxy-1-isopropyl-3,6-dimethyl-7-oxo-heptyl ester
• CAS No.: 916912-86-2
• Molecular Formula: C₂₄H₄₁NO₆S
• Molecular Weight: 471.659

Synonyms:Acetic acid (1S,3S,5S,6S)-7-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-hydroxy-1-isopropyl-3,6-dimethyl-7-oxo-heptyl ester

Chemical Property of Acetic acid (1S,3S,5S,6S)-7-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-hydroxy-1-isopropyl-3,6-dimethyl-7-oxo-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1S,3S,5S,6S)-7-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-hydroxy-1-isopropyl-3,6-dimethyl-7-oxo-heptyl ester

There total 1 articles about Acetic acid (1S,3S,5S,6S)-7-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-hydroxy-1-isopropyl-3,6-dimethyl-7-oxo-heptyl 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)-4-hydroxy-5-methylhexan-2-one (38836-21-4,65651-63-0) → Acetic acid (1S,3S,5S,6S)-7-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-5-hydroxy-1-isopropyl-3,6-dimethyl-7-oxo-heptyl ester (916912-86-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 42.55 g / imidazole / dimethylformamide / 24 h

2.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C

2.2: hexane; tetrahydrofuran / 1 h / -78 °C

3.1: 13.85 g / aq. HF / acetonitrile / 20 °C

4.1: H₂ / Pd/C / methanol / 12 h / 20 °C / 760 Torr

5.1: 3.69 g / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

6.1: pyridine / CH₂Cl₂ / 0 °C

7.1: aq. K₂CO₃ / methanol / 5 h

8.1: 3.64 mg / Dess-Martin reagent / CH₂Cl₂ / 3 h / 0 °C

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

9.2: 88 percent / TiCl₄ / hexane; CH₂Cl₂ / 2 h

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; triethyl borane; trifluorormethanesulfonic acid; hydrogen fluoride; hydrogen; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.2: Peterson reaction / 8.1: Dess-Martin oxidation;

DOI:10.1002/chem.200600599

Reference yield:

Acetic acid (1S,3S,5S,6S)-7-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-5-hydroxy-1-isopropyl-3,6-dimethyl-7-oxo-heptyl ester (916912-86-2) → (E)-(2S,3S,5S,7S,10S,16S,19S,22S,27S)-16-((S)-sec-Butyl)-3-hydroxy-7-isopropyl-22-(4-methoxy-benzyl)-2,5,17,19,20,25-hexamethyl-8,29-dioxa-14,17,20,23,30-pentaaza-tricyclo[25.2.1.010,14]triaconta-1(30),25-diene-9,15,18,21,24-pentaone

Guidance literature:

Multi-step reaction with 12 steps

1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

2: PPTs / 24 h

3: 82 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene

4: TsOH / methanol

5: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h

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

7: HATU; DIPEA / CH₂Cl₂ / 24 h

8: 69 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 3 h / -78 °C

9: N-methylaniline / [Pd(PPh₃)4] / tetrahydrofuran / 2 h

10: HATU; DIPEA / CH₂Cl₂ / 48 h / 20 °C

11: tetrabutylammonium fluoride / tetrahydrofuran

12: HATU; DIPEA / CH₂Cl₂

With dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; diethylamino-sulfur trifluoride; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-methylaniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; sodium hypochlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1002/chem.200600599

Reference yield:

Acetic acid (1S,3S,5S,6S)-7-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-5-hydroxy-1-isopropyl-3,6-dimethyl-7-oxo-heptyl ester (916912-86-2) → pyrrolidine-2-carboxylic acid 6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-oxazol-2-yl)-5-hydroxy-1-isopropyl-3-methyl-heptyl ester

Guidance literature:

Multi-step reaction with 11 steps

1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

2: PPTs / 24 h

3: 82 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene

4: TsOH / methanol

5: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h

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

7: HATU; DIPEA / CH₂Cl₂ / 24 h

8: 69 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 3 h / -78 °C

9: N-methylaniline / [Pd(PPh₃)4] / tetrahydrofuran / 2 h

10: HATU; DIPEA / CH₂Cl₂ / 48 h / 20 °C

11: tetrabutylammonium fluoride / tetrahydrofuran

With dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; diethylamino-sulfur trifluoride; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-methylaniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; sodium hypochlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1002/chem.200600599

upstream raw materials:

(S)-4-hydroxy-5-methylhexan-2-one

Downstream raw materials:

C₆₄H₉₁N₅O₁₂Si

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