DL-(1α,2α,4α,5β,6α,7α)-6-Brom-3-(phenylsulfonyl)-8-oxa-3-azatricyclo<5.1.0.0^2,4>octan-5-ol

Base Information

• Chemical Name: DL-(1α,2α,4α,5β,6α,7α)-6-Brom-3-(phenylsulfonyl)-8-oxa-3-azatricyclo<5.1.0.0^2,4>octan-5-ol
• CAS No.: 112346-57-3
• Molecular Formula: C₁₂H₁₂BrNO₄S
• Molecular Weight: 346.202

Synonyms:DL-(1α,2α,4α,5β,6α,7α)-6-Brom-3-(phenylsulfonyl)-8-oxa-3-azatricyclo<5.1.0.0^2,4>octan-5-ol

Chemical Property of DL-(1α,2α,4α,5β,6α,7α)-6-Brom-3-(phenylsulfonyl)-8-oxa-3-azatricyclo<5.1.0.0^2,4>octan-5-ol

Chemical Property:

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Technology Process of DL-(1α,2α,4α,5β,6α,7α)-6-Brom-3-(phenylsulfonyl)-8-oxa-3-azatricyclo<5.1.0.0^2,4>octan-5-ol

There total 4 articles about DL-(1α,2α,4α,5β,6α,7α)-6-Brom-3-(phenylsulfonyl)-8-oxa-3-azatricyclo<5.1.0.0^2,4>octan-5-ol 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: 100.0%

N-((1R,2R,3S,4R,5S,6S)-2,5-Dibromo-4-hydroxy-7-oxa-bicyclo[4.1.0]hept-3-yl)-benzenesulfonamide (76670-65-0) → (1S,2S,4S,5S,6R,7R)-8-Benzenesulfonyl-5-bromo-3-oxa-8-aza-tricyclo[5.1.0.02,4]octan-6-ol (76670-67-2,112346-57-3)

Guidance literature:

With 2,6-dichloro-benzonitrile; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(00)78718-1

Reference yield:

chloramine-B (127-52-6) + (1α,2α,5α,6α)-2,5-Dibrom-7-oxabicyclo<4.1.0>hept-3-en (39573-55-2) → DL-(1α,2α,4α,5β,6α,7α)-6-Brom-3-(phenylsulfonyl)-8-oxa-3-azatricyclo<5.1.0.02,4>octan-5-ol (112346-57-3)

Guidance literature:

With tert.-butylhydroperoxide; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride; In chloroform; tert-butyl alcohol; at 60 ℃; for 24h;

Reference yield:

chloramine-B (127-52-6) → (1S,2S,4S,5S,6R,7R)-8-Benzenesulfonyl-5-bromo-3-oxa-8-aza-tricyclo[5.1.0.02,4]octan-6-ol (76670-67-2,112346-57-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 15 percent / 25 h / 60 °C

2: 100 percent / DBN / tetrahydrofuran / 20 °C

With 2,6-dichloro-benzonitrile; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)78718-1

upstream raw materials:

N-((1R,2R,3S,4R,5S,6S)-2,5-Dibromo-4-hydroxy-7-oxa-bicyclo[4.1.0]hept-3-yl)-benzenesulfonamide

chloramine-B

(1α,2α,5α,6α)-2,5-Dibrom-7-oxabicyclo<4.1.0>hept-3-en

Downstream raw materials:

(1α,2α,4α,5α,7α,8α)-9-(Phenylsulfonyl)-3,6-dioxa-9-azatetracyclo<6.1.0.0^2,4.0^5,7>nonan

DL-(1α,2α,4α,5β,6α,7α)-6-Brom-3-(phenylsulfonyl)-8-oxa-3-azatricyclo<5.1.0.0^2,4>octan-5-ol-(4-methylphenylsulfonat)

DL-(1α,2α,4α,5β,6α,7α)-6-Brom-3-(phenylsulfonyl)-8-oxa-3-azatricyclo<5.1.0.0^2,4>octan-5-ol-acetat

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