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

Base Information

• Chemical Name: DL-(1α,2α,3β,5β,6α,7α)-6-<(4-Methylphenylsulfonyl)amino>-4,8-dioxatricyclo<5.1.0.0^3,5>octan-2-ol
• CAS No.: 112297-38-8
• Molecular Formula: C₁₃H₁₅NO₅S
• Molecular Weight: 297.332

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

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

Chemical Property:

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

There total 3 articles about DL-(1α,2α,3β,5β,6α,7α)-6-<(4-Methylphenylsulfonyl)amino>-4,8-dioxatricyclo<5.1.0.0^3,5>octan-2-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: 90.0%

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,3β,5β,6α,7α)-6-<(4-Methylphenylsulfonyl)amino>-4,8-dioxatricyclo<5.1.0.03,5>octan-2-ol (112297-38-8) + DL-(1α,2α,4α,5α,6β,7α)-6-<(4-Methylphenylsulfonyl)amino>-3,8-dioxatricyclo<5.1.0.02,4>octan-5-ol (112297-37-7)

Guidance literature:

With potassium hydroxide; In methanol; at 0 ℃; for 5h; Yields of byproduct given;

Reference yield: 83.0%

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,3β,5β,6α,7α)-6-<(4-Methylphenylsulfonyl)amino>-4,8-dioxatricyclo<5.1.0.03,5>octan-2-ol (112297-38-8)

Guidance literature:

With potassium hydroxide; In methanol; 1.) overnight, 0 deg C; 2.) 10 min, reflux;

Reference yield:

DL-(1α,2α,3β,6β)-2-Brom-6-<(4-methylphenylsulfonyl)amino>-4-cyclohexen-1,3-diol (112346-61-9) → DL-(1α,2α,3β,5β,6α,7α)-6-<(4-Methylphenylsulfonyl)amino>-4,8-dioxatricyclo<5.1.0.03,5>octan-2-ol (112297-38-8)

Guidance literature:

Multi-step reaction with 2 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

With potassium hydroxide; dipotassium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

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

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

Downstream raw materials:

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

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

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