(1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

Base Information

• Chemical Name: (1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene
• CAS No.: 163082-04-0
• Molecular Formula: C₁₆H₁₈BrNO₄S
• Molecular Weight: 400.293
• Mol file: 163082-04-0.mol

Synonyms:(1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

Chemical Property of (1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

There total 7 articles about (1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene 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:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene (67451-62-1,82683-92-9,132958-32-8,130792-45-9) → (1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene (163082-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / acetone / 20 °C

2: Cu(acac)2 / acetonitrile / 0 - 20 °C

With toluene-4-sulfonic acid; copper acetylacetonate; In acetone; acetonitrile;

DOI:10.1139/V06-078

Reference yield:

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole (130669-75-9) → (1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene (163082-04-0)

Guidance literature:

Multi-step reaction with 5 steps

1: NBS, H₂O / 1,2-dimethoxy-ethane / 10 h / 0 °C

2: NaN₃ / dimethylsulfoxide

3: Et₃N / CH₂Cl₂

4: LiAlH₄ / tetrahydrofuran

5: Et₃N / CH₂Cl₂

With N-Bromosuccinimide; lithium aluminium tetrahydride; sodium azide; water; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ja960596j

Reference yield:

(1R,2S,5S,6R)-3,6-dibromo-1,2-O-isopropylidenecyclohex-3-ene-1,2,5-triol (183674-17-1) → (1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene (163082-04-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NaN₃ / dimethylsulfoxide

2: Et₃N / CH₂Cl₂

3: LiAlH₄ / tetrahydrofuran

4: Et₃N / CH₂Cl₂

With lithium aluminium tetrahydride; sodium azide; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ja960596j

upstream raw materials:

p-toluenesulfonyl chloride

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

(1R,2S,5S,6R)-3,6-dibromo-1,2-O-isopropylidenecyclohex-3-ene-1,2,5-triol

Downstream raw materials:

N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide

N-[(3aS,4R,5S,7aS)-5-azido-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-yl]-4-methylbenzenesulfonamide

(3aS,4S,5R,6R,7R,7aS)-4-hydroxy-2,2-dimethyl-7-(4-methylphenylsulfonamido)-5-phenylcarbonyloxy-6-(2-trimethylsilyl-1-ethynyl)perhydro-1,3-benzodioxole

(3aS,4S,5R,6R,7R,7aS)-4-hydroxy-2,2-dimethyl-7-(4-methylphenylsulfonamido)-5-phenylcarbonyloxy-6-(1-ethynyl)perhydro-1,3-benzodioxole