DL-(1α,2α,4α,5β,7β,8α)-9-(4-Methylphenylsulfonyl)-3,6-dioxa-9-azatetracyclo<6.1.0.0^2,40^5.7>nonan

Base Information

• Chemical Name: DL-(1α,2α,4α,5β,7β,8α)-9-(4-Methylphenylsulfonyl)-3,6-dioxa-9-azatetracyclo<6.1.0.0^2,40^5.7>nonan
• CAS No.: 112419-19-9
• Molecular Formula: C₁₃H₁₃NO₄S
• Molecular Weight: 279.317

Synonyms:DL-(1α,2α,4α,5β,7β,8α)-9-(4-Methylphenylsulfonyl)-3,6-dioxa-9-azatetracyclo<6.1.0.0^2,40^5.7>nonan

Chemical Property of DL-(1α,2α,4α,5β,7β,8α)-9-(4-Methylphenylsulfonyl)-3,6-dioxa-9-azatetracyclo<6.1.0.0^2,40^5.7>nonan

Chemical Property:

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Technology Process of DL-(1α,2α,4α,5β,7β,8α)-9-(4-Methylphenylsulfonyl)-3,6-dioxa-9-azatetracyclo<6.1.0.0^2,40^5.7>nonan

There total 4 articles about DL-(1α,2α,4α,5β,7β,8α)-9-(4-Methylphenylsulfonyl)-3,6-dioxa-9-azatetracyclo<6.1.0.0^2,40^5.7>nonan 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: 27.0%

DL-(1α,2α,3β,5β,6α,7α)-6-<(4-Methylphenylsulfonyl)amino>-4,8-dioxatricyclo<5.1.0.03,5>octan-2-ol-methansulfonat (112297-39-9) → DL-(1α,2α,4α,5β,7β,8α)-9-(4-Methylphenylsulfonyl)-3,6-dioxa-9-azatetracyclo<6.1.0.02,405.7>nonan (112419-19-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 70 ℃; for 12h;

Reference yield:

DL-(1α,2α,3β,6β)-2-Brom-6-<(4-methylphenylsulfonyl)amino>-4-cyclohexen-1,3-diol (112346-61-9) → DL-(1α,2α,4α,5β,7β,8α)-9-(4-Methylphenylsulfonyl)-3,6-dioxa-9-azatetracyclo<6.1.0.02,405.7>nonan (112419-19-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / m-chloroperbenzoic acid, K₂HPO₄ / tetrahydrofuran; CH₂Cl₂ / 6 h / Heating

2: 83 percent / 5percent KOH / methanol / 1.) overnight, 0 deg C; 2.) 10 min, reflux

3: 90 percent / NEt₃ / CH₂Cl₂ / 3 h / 0 °C

4: 27 percent / NaH / dimethylformamide / 12 h / 70 °C

With potassium hydroxide; dipotassium hydrogenphosphate; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

DL-(1α,2β,3α,4α,5β,6α)-3-Brom-5-<(4-methylphenylsulfonyl)amino>-7-oxabicyclo<4.1.0>heptan-2,4-diol (112297-34-4) → DL-(1α,2α,4α,5β,7β,8α)-9-(4-Methylphenylsulfonyl)-3,6-dioxa-9-azatetracyclo<6.1.0.02,405.7>nonan (112419-19-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / 5percent KOH / methanol / 1.) overnight, 0 deg C; 2.) 10 min, reflux

2: 90 percent / NEt₃ / CH₂Cl₂ / 3 h / 0 °C

3: 27 percent / NaH / dimethylformamide / 12 h / 70 °C

With potassium hydroxide; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

DL-(1α,2α,3β,5β,6α,7α)-6-<(4-Methylphenylsulfonyl)amino>-4,8-dioxatricyclo<5.1.0.0^3,5>octan-2-ol-methansulfonat

DL-(1α,2α,3β,6β)-2-Brom-6-<(4-methylphenylsulfonyl)amino>-4-cyclohexen-1,3-diol

DL-(1α,2α,3β,5β,6α,7α)-6-<(4-Methylphenylsulfonyl)amino>-4,8-dioxatricyclo<5.1.0.0^3,5>octan-2-ol

DL-(1α,2β,3α,4α,5β,6α)-3-Brom-5-<(4-methylphenylsulfonyl)amino>-7-oxabicyclo<4.1.0>heptan-2,4-diol

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