(3S,5S)-{2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]isoxazolidin-5-yl}-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Base Information

• Chemical Name: (3S,5S)-{2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]isoxazolidin-5-yl}-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone
• CAS No.: 455942-08-2
• Molecular Formula: C₂₆H₃₆N₂O₆S
• Molecular Weight: 504.648

Synonyms:

Chemical Property of (3S,5S)-{2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]isoxazolidin-5-yl}-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-{2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]isoxazolidin-5-yl}-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

There total 1 articles about (3S,5S)-{2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]isoxazolidin-5-yl}-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone 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: 56.0%

acrylcamphorsultam (94594-91-9) + N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → [(3S,5R)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-isoxazolidin-5-yl]-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone + [(3R,5S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-isoxazolidin-5-yl]-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone + (3S,5S)-{2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]isoxazolidin-5-yl}-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]dec-4-yl)-methanone (455942-08-2)

Guidance literature:

In toluene; Heating;

DOI:10.1016/S0957-4166(02)00088-5

Reference yield:

(3S,5S)-{2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]isoxazolidin-5-yl}-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]dec-4-yl)-methanone (455942-08-2) → benzoic acid (3S,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-pyrrolidin-3-yl ester (455942-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / H₂ / Pd(OH)2/C / methanol / 24 h / 20 °C / 103430 Torr

2: 85 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

With pyridine; hydrogen; palladium dihydroxide; In methanol; dichloromethane;

DOI:10.1016/S0957-4166(02)00088-5

Reference yield:

(3S,5S)-{2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]isoxazolidin-5-yl}-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]dec-4-yl)-methanone (455942-08-2) → (2S,4S)-4-(benzyloxy)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:

Multi-step reaction with 5 steps

1.1: 88 percent / H₂ / Pd(OH)2/C / methanol / 24 h / 20 °C / 103430 Torr

2.1: 85 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

3.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

4.1: HIO₄ / diethyl ether / 4 h / 20 °C

4.2: NaClO₂; NaH₂PO₄; 35 percent H₂O₂ / 1 h / 10 °C

5.1: 0.218 g / diethyl ether / 0.08 h / 0 °C

With pyridine; dmap; hydrogen; periodic acid; triethylamine; palladium dihydroxide; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0957-4166(02)00088-5

upstream raw materials:

acrylcamphorsultam

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

Downstream raw materials:

benzoic acid (3S,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-pyrrolidin-3-yl ester

(3S,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(benzoyloxy)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

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