[3aR-[(3aR*,4R*,6aS*),3aα,6α,7aβ]]-3H-3a,6-methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-4-[[tetrahydro-1,3-dioxolo-5-(phenylmethyl)-2-oxo-[4,5-c]-pyrrol-4-yl]carbonyl]-2,2-dioxide

Base Information

• Chemical Name: [3aR-[(3aR*,4R*,6aS*),3aα,6α,7aβ]]-3H-3a,6-methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-4-[[tetrahydro-1,3-dioxolo-5-(phenylmethyl)-2-oxo-[4,5-c]-pyrrol-4-yl]carbonyl]-2,2-dioxide
• CAS No.: 332041-84-6
• Molecular Formula: C₂₃H₂₈N₂O₆S
• Molecular Weight: 460.551

Synonyms:

Chemical Property of [3aR-[(3aR*,4R*,6aS*),3aα,6α,7aβ]]-3H-3a,6-methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-4-[[tetrahydro-1,3-dioxolo-5-(phenylmethyl)-2-oxo-[4,5-c]-pyrrol-4-yl]carbonyl]-2,2-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3aR-[(3aR*,4R*,6aS*),3aα,6α,7aβ]]-3H-3a,6-methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-4-[[tetrahydro-1,3-dioxolo-5-(phenylmethyl)-2-oxo-[4,5-c]-pyrrol-4-yl]carbonyl]-2,2-dioxide

There total 3 articles about [3aR-[(3aR*,4R*,6aS*),3aα,6α,7aβ]]-3H-3a,6-methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-4-[[tetrahydro-1,3-dioxolo-5-(phenylmethyl)-2-oxo-[4,5-c]-pyrrol-4-yl]carbonyl]-2,2-dioxide 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: 22.0%

vinylene carbonate (872-36-6) + ((R)-1-Benzyl-aziridin-2-yl)-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (153440-80-3) → (+)-camphorsultam (108448-77-7,124224-04-0) + (1-Benzyl-1H-pyrrol-2-yl)-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone + [3aR-[(3aR*,4R*,6aS*),3aα,6α,7aβ]]-3H-3a,6-methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-4-[[tetrahydro-1,3-dioxolo-5-(phenylmethyl)-2-oxo-[4,5-c]-pyrrol-4-yl]carbonyl]-2,2-dioxide (332041-84-6) + [3aR-[(3aS*,4S*,6aR*),3aα,6α,7aβ]]-3H-3a,6-methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-4-[[tetrahydro-1,3-dioxolo-5-(phenylmethyl)-2-oxo-[4,5-c]-pyrrol-4-yl]carbonyl]-2,2-dioxide (332041-85-7)

Guidance literature:

In toluene; at 195 - 197 ℃; for 15h;

DOI:10.1016/S0040-4020(00)00998-4

Reference yield:

(2S)-N-(acryloyl)bornane-10,2-sultam (119944-89-7) → [3aR-[(3aR*,4R*,6aS*),3aα,6α,7aβ]]-3H-3a,6-methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-4-[[tetrahydro-1,3-dioxolo-5-(phenylmethyl)-2-oxo-[4,5-c]-pyrrol-4-yl]carbonyl]-2,2-dioxide (332041-84-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Br₂ / CHCl₃ / 1 h / 50 °C

2: Et₃N / CHCl₃ / 50 °C

3: toluene / 15 h / 195 - 197 °C

With bromine; triethylamine; In chloroform; toluene;

DOI:10.1016/S0040-4020(00)00998-4

Reference yield:

(1R,2S,4S)-N-(2,3-dibromopropionyl)-bornane-2,10-sultam (635678-42-1) → [3aR-[(3aR*,4R*,6aS*),3aα,6α,7aβ]]-3H-3a,6-methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-4-[[tetrahydro-1,3-dioxolo-5-(phenylmethyl)-2-oxo-[4,5-c]-pyrrol-4-yl]carbonyl]-2,2-dioxide (332041-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CHCl₃ / 50 °C

2: toluene / 15 h / 195 - 197 °C

With triethylamine; In chloroform; toluene;

DOI:10.1016/S0040-4020(00)00998-4

upstream raw materials:

vinylene carbonate

((R)-1-Benzyl-aziridin-2-yl)-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

(2S)-N-(acryloyl)bornane-10,2-sultam

(1R,2S,4S)-N-(2,3-dibromopropionyl)-bornane-2,10-sultam

Downstream raw materials:

(2R)-N-{N-[bis(methylthio)methylidene]glycyl}bornane-10,2-sultam

(+)-camphorsultam

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