DL-(1α,2α,3α,5α,6β,7α,8α)-2-(4-Methylphenylsulfonyloxy)-4-(phenylsulfonyl)-6-(phenylsulfonylamino)-4-azatricyclo<5.1.0.0^3,5>octan-8-carbonsaeure-methylester

Base Information

• Chemical Name: DL-(1α,2α,3α,5α,6β,7α,8α)-2-(4-Methylphenylsulfonyloxy)-4-(phenylsulfonyl)-6-(phenylsulfonylamino)-4-azatricyclo<5.1.0.0^3,5>octan-8-carbonsaeure-methylester
• CAS No.: 112297-65-1
• Molecular Formula: C₂₈H₂₈N₂O₉S₃
• Molecular Weight: 632.736

Synonyms:

Chemical Property of DL-(1α,2α,3α,5α,6β,7α,8α)-2-(4-Methylphenylsulfonyloxy)-4-(phenylsulfonyl)-6-(phenylsulfonylamino)-4-azatricyclo<5.1.0.0^3,5>octan-8-carbonsaeure-methylester

Chemical Property:

Purity/Quality:

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Technology Process of DL-(1α,2α,3α,5α,6β,7α,8α)-2-(4-Methylphenylsulfonyloxy)-4-(phenylsulfonyl)-6-(phenylsulfonylamino)-4-azatricyclo<5.1.0.0^3,5>octan-8-carbonsaeure-methylester

There total 6 articles about DL-(1α,2α,3α,5α,6β,7α,8α)-2-(4-Methylphenylsulfonyloxy)-4-(phenylsulfonyl)-6-(phenylsulfonylamino)-4-azatricyclo<5.1.0.0^3,5>octan-8-carbonsaeure-methylester 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: 15.0%

DL-(1α,2α,3β,4α,5β,6α,7α)-2,4-Bis(4-methylphenylsulfonyloxy)-3,5-bis(phenylsulfonylamino)bicyclo<4.1.0>heptan-7-carbonsaeure-methylester (112297-63-9) → (1α,2α,4α,5α,7α,8α,9α)-3,6-Bis(phenylsulfonyl)-3,6-diazatetracyclo<6.1.0.02,4.05,7>nonan-9-carbonsaeure-methylester (112346-65-3) + DL-(1α,2α,3α,5α,6β,7α,8α)-2-(4-Methylphenylsulfonyloxy)-4-(phenylsulfonyl)-6-(phenylsulfonylamino)-4-azatricyclo<5.1.0.03,5>octan-8-carbonsaeure-methylester (112297-65-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 1h;

Reference yield:

(1RS,2RS,4RS,5SR,7SR,8SR)-methyl 3,6-dioxatetracyclo[6.1.0.02,4.05,7]nonane-9-carboxylate (53343-62-7) → DL-(1α,2α,3α,5α,6β,7α,8α)-2-(4-Methylphenylsulfonyloxy)-4-(phenylsulfonyl)-6-(phenylsulfonylamino)-4-azatricyclo<5.1.0.03,5>octan-8-carbonsaeure-methylester (112297-65-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / MgCl₂*6H₂O, NaN₃ / methanol / 20 h / Heating

2: 100 percent / H₂ / Pd/C / methanol / 4 h / 760 Torr / Ambient temperature

3: 53 percent / NaOH / dioxane; H₂O / Ambient temperature

4: 82 percent / pyridine; benzene / 12 h

5: 15 percent / tert-BuOK / tetrahydrofuran / 1 h

With sodium hydroxide; sodium azide; potassium tert-butylate; hydrogen; magnesium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; benzene;

Reference yield:

DL-(1α,2α,3β,4α,5β,6α,7α)-3,5-Diazido-2,4-dihydroxybicyclo<4.1.0>heptan-7-carbonsaeure-methylester (112297-49-1) → DL-(1α,2α,3α,5α,6β,7α,8α)-2-(4-Methylphenylsulfonyloxy)-4-(phenylsulfonyl)-6-(phenylsulfonylamino)-4-azatricyclo<5.1.0.03,5>octan-8-carbonsaeure-methylester (112297-65-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / H₂ / Pd/C / methanol / 4 h / 760 Torr / Ambient temperature

2: 53 percent / NaOH / dioxane; H₂O / Ambient temperature

3: 82 percent / pyridine; benzene / 12 h

4: 15 percent / tert-BuOK / tetrahydrofuran / 1 h

With sodium hydroxide; potassium tert-butylate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; benzene;

upstream raw materials:

(1R,2S,3R,4R,5S,6S)-2,4-Bis-benzenesulfonylamino-3,5-bis-(toluene-4-sulfonyloxy)-bicyclo[4.1.0]heptane-7-carboxylic acid methyl ester

DL-(1α,2α,3β,4α,5β,6α,7α)-2,4-Bis(4-methylphenylsulfonyloxy)-3,5-bis(phenylsulfonylamino)bicyclo<4.1.0>heptan-7-carbonsaeure-methylester

(1RS,2RS,4RS,5SR,7SR,8SR)-methyl 3,6-dioxatetracyclo[6.1.0.0^2,4.0^5,7]nonane-9-carboxylate

DL-(1α,2α,3β,4α,5β,6α,7α)-3,5-Diamino-2,4-dihydroxybicyclo<4.1.0>heptan-7-carbonsaeure-methylester

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