(1R,3aS,5S,7aS)-4-(Benzyl-trimethylsilanylmethyl-amino)-5-((S)-1-hydroxy-propyl)-1-oxo-2-((R)-1-phenyl-ethyl)-1,2,3a,4,5,7a-hexahydro-1λ⁴-isothiazolo[4,5-b]pyridin-3-one

Base Information

• Chemical Name: (1R,3aS,5S,7aS)-4-(Benzyl-trimethylsilanylmethyl-amino)-5-((S)-1-hydroxy-propyl)-1-oxo-2-((R)-1-phenyl-ethyl)-1,2,3a,4,5,7a-hexahydro-1λ⁴-isothiazolo[4,5-b]pyridin-3-one
• CAS No.: 816452-89-8
• Molecular Formula: C₂₈H₃₉N₃O₃SSi
• Molecular Weight: 525.787

Synonyms:(1R,3aS,5S,7aS)-4-(Benzyl-trimethylsilanylmethyl-amino)-5-((S)-1-hydroxy-propyl)-1-oxo-2-((R)-1-phenyl-ethyl)-1,2,3a,4,5,7a-hexahydro-1λ⁴-isothiazolo[4,5-b]pyridin-3-one

Chemical Property of (1R,3aS,5S,7aS)-4-(Benzyl-trimethylsilanylmethyl-amino)-5-((S)-1-hydroxy-propyl)-1-oxo-2-((R)-1-phenyl-ethyl)-1,2,3a,4,5,7a-hexahydro-1λ⁴-isothiazolo[4,5-b]pyridin-3-one

Chemical Property:

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Technology Process of (1R,3aS,5S,7aS)-4-(Benzyl-trimethylsilanylmethyl-amino)-5-((S)-1-hydroxy-propyl)-1-oxo-2-((R)-1-phenyl-ethyl)-1,2,3a,4,5,7a-hexahydro-1λ⁴-isothiazolo[4,5-b]pyridin-3-one

There total 4 articles about (1R,3aS,5S,7aS)-4-(Benzyl-trimethylsilanylmethyl-amino)-5-((S)-1-hydroxy-propyl)-1-oxo-2-((R)-1-phenyl-ethyl)-1,2,3a,4,5,7a-hexahydro-1λ⁴-isothiazolo[4,5-b]pyridin-3-one 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: 50.0%

N-benzyl-N'-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allylidene]-N-trimethylsilanylmethyl-hydrazine + propionaldehyde (123-38-6) + (R)-1-Oxo-2-((R)-1-phenyl-ethyl)-1,2-dihydro-1λ4-isothiazol-3-one (700380-06-9) → (1R,3aS,5S,7aS)-4-(Benzyl-trimethylsilanylmethyl-amino)-5-((S)-1-hydroxy-propyl)-1-oxo-2-((R)-1-phenyl-ethyl)-1,2,3a,4,5,7a-hexahydro-1λ4-isothiazolo[4,5-b]pyridin-3-one (816452-89-8)

Guidance literature:

N-benzyl-N'-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allylidene]-N-trimethylsilanylmethyl-hydrazine; propionaldehyde; (R)-1-Oxo-2-((R)-1-phenyl-ethyl)-1,2-dihydro-1λ⁴-isothiazol-3-one; In toluene; at 80 ℃; for 70h;

With sodium hydrogencarbonate; In water; toluene; at 20 ℃; for 0.5h;

DOI:10.1021/jo048581o

Reference yield:

2-((R)-1-Phenyl-ethyl)-isothiazol-3-one → (1R,3aS,5S,7aS)-4-(Benzyl-trimethylsilanylmethyl-amino)-5-((S)-1-hydroxy-propyl)-1-oxo-2-((R)-1-phenyl-ethyl)-1,2,3a,4,5,7a-hexahydro-1λ4-isothiazolo[4,5-b]pyridin-3-one (816452-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3.8 g / m-chloroperoxybenzoic acid / CH₂Cl₂ / 3 h / 0 °C

2.1: toluene / 70 h / 80 °C

2.2: 50 percent / NaHCO₃ / H₂O; toluene / 0.5 h / 20 °C

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene;

DOI:10.1021/jo048581o

Reference yield:

C11H18N2OSi (1026552-54-4) → (1R,3aS,5S,7aS)-4-(Benzyl-trimethylsilanylmethyl-amino)-5-((S)-1-hydroxy-propyl)-1-oxo-2-((R)-1-phenyl-ethyl)-1,2,3a,4,5,7a-hexahydro-1λ4-isothiazolo[4,5-b]pyridin-3-one (816452-89-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiAlH₄ / diethyl ether / 4 h / 0 - 20 °C

2.1: MgSO₄ / CH₂Cl₂ / 2 h / 40 °C

3.1: toluene / 70 h / 80 °C

3.2: 50 percent / NaHCO₃ / H₂O; toluene / 0.5 h / 20 °C

With lithium aluminium tetrahydride; magnesium sulfate; In diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo048581o

upstream raw materials:

propionaldehyde

(R)-1-Oxo-2-((R)-1-phenyl-ethyl)-1,2-dihydro-1λ⁴-isothiazol-3-one

N-benzyl-N-trimethylsilanylmethyl-hydrazine

C₁₁H₁₈N₂OSi

Downstream raw materials:

(2R,6S)-1-(Benzyl-trimethylsilanylmethyl-amino)-6-((S)-1-hydroxy-propyl)-1,2,5,6-tetrahydro-pyridine-2-carboxylic acid ((R)-1-phenyl-ethyl)-amide

C₁₈H₂₁N₃O₄

(1S,5R,8aS)-1-Ethyl-3-oxo-1,5,8,8a-tetrahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ((R)-1-phenyl-ethyl)-amide

(2R,6S)-6-((S)-1-Hydroxy-propyl)-1,2,5,6-tetrahydro-pyridine-2-carboxylic acid ((R)-1-phenyl-ethyl)-amide

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