<3aS<1<1S^*,3(R^*,S^*),5R^*,6R^*>,3aα,6α,7aβ>>-8-Methyl-2,4-dioxo-α-phenyl-6-<(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)carbonyl>-3,8-diazabicyclo<3.2.1>octane 3-acetic acid methyl ester S,S-dioxide

Base Information

• Chemical Name: <3aS<1<1S^*,3(R^*,S^*),5R^*,6R^*>,3aα,6α,7aβ>>-8-Methyl-2,4-dioxo-α-phenyl-6-<(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)carbonyl>-3,8-diazabicyclo<3.2.1>octane 3-acetic acid methyl ester S,S-dioxide
• CAS No.: 127381-62-8
• Molecular Formula: C₂₇H₃₃N₃O₇S
• Molecular Weight: 543.641
• Mol file: 127381-62-8.mol

Synonyms:

Chemical Property of <3aS<1<1S^*,3(R^*,S^*),5R^*,6R^*>,3aα,6α,7aβ>>-8-Methyl-2,4-dioxo-α-phenyl-6-<(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)carbonyl>-3,8-diazabicyclo<3.2.1>octane 3-acetic acid methyl ester S,S-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3aS<1<1S^*,3(R^*,S^*),5R^*,6R^*>,3aα,6α,7aβ>>-8-Methyl-2,4-dioxo-α-phenyl-6-<(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)carbonyl>-3,8-diazabicyclo<3.2.1>octane 3-acetic acid methyl ester S,S-dioxide

There total 6 articles about <3aS<1<1S^*,3(R^*,S^*),5R^*,6R^*>,3aα,6α,7aβ>>-8-Methyl-2,4-dioxo-α-phenyl-6-<(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)carbonyl>-3,8-diazabicyclo<3.2.1>octane 3-acetic acid methyl ester S,S-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: 61.0%

(+/-)-6-Methyl-2,4-dioxo-α-phenyl-3,6-diazabicyclo<3.1.0>hexane-3-acetic acid methyl ester (120566-71-4,127420-40-0) + acrylcamphorsultam (94594-91-9) → [(1S,5R,6S)-6-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-8-methyl-2,4-dioxo-3,8-diaza-bicyclo[3.2.1]oct-3-yl]-phenyl-acetic acid methyl ester (127381-62-8,127420-42-2)

Guidance literature:

In 1,4-dioxane; Irradiation;

DOI:10.1021/jo00300a004

Reference yield: 61.0%

(+/-)-6-Methyl-2,4-dioxo-α-phenyl-3,6-diazabicyclo<3.1.0>hexane-3-acetic acid methyl ester (120566-71-4,127420-40-0) + acrylcamphorsultam (94594-91-9) → <3aS<1<1S*,3(R*,S*),5R*,6R*>,3aα,6α,7aβ>>-8-Methyl-2,4-dioxo-α-phenyl-6-<(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)carbonyl>-3,8-diazabicyclo<3.2.1>octane 3-acetic acid methyl ester S,S-dioxide (127381-62-8,127420-42-2)

Guidance literature:

In 1,4-dioxane; Irradiation; repeated portionwise addition of dipolarophile;

DOI:10.1021/jo00020a035

Reference yield:

(S)-Phenylglycine methyl ester (6591-61-3,24461-61-8,26682-99-5,37760-98-8) → <3aS<1<1S*,3(R*,S*),5R*,6R*>,3aα,6α,7aβ>>-8-Methyl-2,4-dioxo-α-phenyl-6-<(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)carbonyl>-3,8-diazabicyclo<3.2.1>octane 3-acetic acid methyl ester S,S-dioxide (127381-62-8,127420-42-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / diethyl ether / 20 h / Ambient temperature

2: 1.) 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / 1.) CH₂Cl₂ or THF, r.t., 20 h, 2.) toluene, 100 deg C, 18 h

3: 91 percent / toluene / 24 h / Ambient temperature

4: 82 percent / dioxane / 5 h / Irradiation

5: 61 percent / dioxane / Irradiation; repeated portionwise addition of dipolarophile

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; diethyl ether; toluene;

DOI:10.1021/jo00020a035

upstream raw materials:

(+/-)-6-Methyl-2,4-dioxo-α-phenyl-3,6-diazabicyclo<3.1.0>hexane-3-acetic acid methyl ester

acrylcamphorsultam

(S)-Phenylglycine methyl ester

(+/-)-α-Phenyl-2,5-dioxo-1H-pyrrole-1-acetic acid methyl ester