(1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol

Base Information

• Chemical Name: (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol
• CAS No.: 483341-80-6
• Molecular Formula: C₂₀H₁₈N₂O₇S
• Molecular Weight: 430.438

Synonyms:(1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol

Chemical Property of (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol

Chemical Property:

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Technology Process of (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol

There total 9 articles about (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol 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: 98.0%

phosgene (75-44-5) + (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-cyclohex-3-ene-1,2-diol (688334-35-2) → (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol (483341-80-6)

Guidance literature:

With pyridine; In dichloromethane; toluene; at 0 ℃; for 2h;

DOI:10.1016/j.tet.2004.01.063

Reference yield:

Carbonic acid (1R,5S,6S)-5-[benzyl-(2-nitro-benzenesulfonyl)-amino]-6-hydroxy-cyclohex-2-enyl ester methyl ester → (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol (483341-80-6)

Guidance literature:

With N-benzyl-2-nitrobenzenesulfonamide; triethylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tet.2004.01.063

Reference yield:

2-Nitrobenzenesulfonyl chloride (1694-92-4) → (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol (483341-80-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / Na₂CO₃ / CH₂Cl₂ / 20 °C

2: Cl₂(PPh₃)2Ru=CHPh / CH₂Cl₂ / 20 °C

3: acetic acid; H₂O / 2 h / Heating

4: 98 percent / pyridine / CH₂Cl₂; toluene / 2 h / 0 °C

With pyridine; RuCl₂(CHPh)(PPh₃)2; sodium carbonate; In dichloromethane; water; acetic acid; toluene;

DOI:10.1016/j.tet.2004.01.063

upstream raw materials:

1,1'-carbonyldiimidazole

(1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-cyclohex-3-ene-1,2-diol

phosgene

methyl chloroformate

Downstream raw materials:

(1R,4R,6S)-4,6-bis[(N-benzyl)-o-nitrobenzenesulfon-amino]-cyclohex-2-enol

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