<3aR-<1<1S^*,3(R^*),5R^*,6R^*>,3aα,6α,7aβ>>-1-<<3-<2-hydroxy-1-(2-methoxy-6-methylphenyl)ethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>oct-6-yl>carbonyl>hexahydro-8,8-dimethyl-2,2-dioxo-3H-3a,6-methano-2,1-benzisothiazole

Base Information

• Chemical Name: <3aR-<1<1S^*,3(R^*),5R^*,6R^*>,3aα,6α,7aβ>>-1-<<3-<2-hydroxy-1-(2-methoxy-6-methylphenyl)ethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>oct-6-yl>carbonyl>hexahydro-8,8-dimethyl-2,2-dioxo-3H-3a,6-methano-2,1-benzisothiazole
• CAS No.: 139527-58-5
• Molecular Formula: C₂₈H₃₇N₃O₇S
• Molecular Weight: 559.684
• Mol file: 139527-58-5.mol

Synonyms:<3aR-<1<1S^*,3(R^*),5R^*,6R^*>,3aα,6α,7aβ>>-1-<<3-<2-hydroxy-1-(2-methoxy-6-methylphenyl)ethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>oct-6-yl>carbonyl>hexahydro-8,8-dimethyl-2,2-dioxo-3H-3a,6-methano-2,1-benzisothiazole

Chemical Property of <3aR-<1<1S^*,3(R^*),5R^*,6R^*>,3aα,6α,7aβ>>-1-<<3-<2-hydroxy-1-(2-methoxy-6-methylphenyl)ethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>oct-6-yl>carbonyl>hexahydro-8,8-dimethyl-2,2-dioxo-3H-3a,6-methano-2,1-benzisothiazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3aR-<1<1S^*,3(R^*),5R^*,6R^*>,3aα,6α,7aβ>>-1-<<3-<2-hydroxy-1-(2-methoxy-6-methylphenyl)ethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>oct-6-yl>carbonyl>hexahydro-8,8-dimethyl-2,2-dioxo-3H-3a,6-methano-2,1-benzisothiazole

There total 14 articles about <3aR-<1<1S^*,3(R^*),5R^*,6R^*>,3aα,6α,7aβ>>-1-<<3-<2-hydroxy-1-(2-methoxy-6-methylphenyl)ethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>oct-6-yl>carbonyl>hexahydro-8,8-dimethyl-2,2-dioxo-3H-3a,6-methano-2,1-benzisothiazole 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%

(2S)-N-(acryloyl)bornane-10,2-sultam (119944-89-7) + 3-[(R)-2-Hydroxy-1-(2-methoxy-6-methyl-phenyl)-ethyl]-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione (139527-57-4) → (1R,5S,6R)-6-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-3-[(R)-2-hydroxy-1-(2-methoxy-6-methyl-phenyl)-ethyl]-8-methyl-3,8-diaza-bicyclo[3.2.1]octane-2,4-dione (139527-58-5)

Guidance literature:

In 1,4-dioxane; Irradiation;

DOI:10.1021/ja00033a089

Reference yield: 54.0%

(2S)-N-(acryloyl)bornane-10,2-sultam (119944-89-7) + (R)-3-<2-hydroxy-1-(2-methoxy-6-methylphenyl)ethyl>-6-methyl-3,6-diazabicyclo<3.1.0>hexane-2,4-dione → <3aR-<1<1S*,3(R*),5R*,6R*>,3aα,6α,7aβ>>-1-<<3-<2-hydroxy-1-(2-methoxy-6-methylphenyl)ethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>oct-6-yl>carbonyl>hexahydro-8,8-dimethyl-2,2-dioxo-3H-3a,6-methano-2,1-benzisothiazole (139527-58-5)

Guidance literature:

In 1,4-dioxane; Irradiation;

DOI:10.1021/ja00076a036

Reference yield:

(2-methoxy-6-methylphenyl)acetic acid (151858-71-8) → <3aR-<1<1S*,3(R*),5R*,6R*>,3aα,6α,7aβ>>-1-<<3-<2-hydroxy-1-(2-methoxy-6-methylphenyl)ethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>oct-6-yl>carbonyl>hexahydro-8,8-dimethyl-2,2-dioxo-3H-3a,6-methano-2,1-benzisothiazole (139527-58-5)

Guidance literature:

Multi-step reaction with 11 steps

1: Et₃N / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) 0 deg C, 45 min

2: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, a) -78 deg C, 15 min, b) RT, 9 h

3: 1.) KN(SiMe₃)2, 2.) trisyl azide, 3.) AcOH

4: 83 percent / NaBH₄ / tetrahydrofuran; H₂O / 42 h / 5 °C

5: 78 percent / H₂ / 10percent Pd/C / ethanol / 24 h / Ambient temperature

6: 80 percent / diethyl ether / 20 h / Ambient temperature

7: 44 percent / 20 h / 120 °C

8: 76 percent / 5N HCl / tetrahydrofuran / 36 h / Ambient temperature

9: 99 percent / toluene / 24 h / Ambient temperature

10: 90 percent / dioxane / 5 h / Irradiation

11: 54 percent / dioxane / Irradiation

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; water; toluene;

DOI:10.1021/ja00076a036

upstream raw materials:

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

3-[(R)-2-Hydroxy-1-(2-methoxy-6-methyl-phenyl)-ethyl]-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione

(2-methoxy-6-methylphenyl)acetic acid

(2R)-2-amino-2-(2-methoxy-6-methylphenyl)ethyl alcohol

Downstream raw materials:

(1R,5S,6R)-6-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-3-[(R)-2-methoxymethoxy-1-(2-methoxy-6-methyl-phenyl)-ethyl]-8-methyl-3,8-diaza-bicyclo[3.2.1]octane-2,4-dione

(-)-quinocarcin

4-cyano-6-hydroxymethyl-3,12-imino-7-methoxy-13-methyl-1,2,3,4,6,11,11a,12-octahydroazepino<1,2-b>isoquinoline-1-carboxylic acid

(1R,5S,6R)-3-[(R)-1-(2-Bromomethyl-6-methoxy-phenyl)-2-methoxymethoxy-ethyl]-6-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-8-methyl-3,8-diaza-bicyclo[3.2.1]octane-2,4-dione