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

Base Information

• Chemical Name: DL-(1α,2α,3β,6β)-2-Brom-6-<(4-methylphenylsulfonyl)amino>-4-cyclohexen-1,3-diol
• CAS No.: 112346-61-9
• Molecular Formula: C₁₃H₁₆BrNO₄S
• Molecular Weight: 362.244

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

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

Chemical Property:

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

There total 3 articles about DL-(1α,2α,3β,6β)-2-Brom-6-<(4-methylphenylsulfonyl)amino>-4-cyclohexen-1,3-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: 92.0%

chloroamine-T (127-65-1) + (+/-)-(3/4,5,6)-4-bromo-5,6-epoxy-3-hydroxycyclohexene (69945-45-5,80582-73-6,129785-51-9,139012-51-4,140696-30-6) → toluene-4-sulfonamide (70-55-3) + DL-(1α,2α,3β,6β)-2-Brom-6-<(4-methylphenylsulfonyl)amino>-4-cyclohexen-1,3-diol (112346-61-9)

Guidance literature:

With zinc(II) sulfate; In methanol; for 1h; Heating;

Reference yield:

(1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol (69945-44-4,80563-10-6) → DL-(1α,2α,3β,6β)-2-Brom-6-<(4-methylphenylsulfonyl)amino>-4-cyclohexen-1,3-diol (112346-61-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / KOH / tetrahydrofuran; methanol / 2 h / 0 °C

2: 92 percent / ZnSO₄ / methanol / 1 h / Heating

With potassium hydroxide; zinc(II) sulfate; In tetrahydrofuran; methanol;

Reference yield:

chloroamine-T (127-65-1) + (1R,2S,3R,6R)-2-bromo-7-oxabicyclo[4.1.0]hept-4-en-3-ol (140696-30-6) → N-((1S,4R,5S,6R)-5-Bromo-4,6-dihydroxy-cyclohex-2-enyl)-4-methyl-benzenesulfonamide (76670-78-5,112346-61-9)

Guidance literature:

In methanol; Yield given; Heating;

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

upstream raw materials:

chloroamine-T

(1R,2S,3R,6R)-2-bromo-7-oxabicyclo[4.1.0]hept-4-en-3-ol

(+/-)-(3/4,5,6)-4-bromo-5,6-epoxy-3-hydroxycyclohexene

(1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol

Downstream raw materials:

N-((1S,2R,3S,6R)-2-Hydroxy-7-oxa-bicyclo[4.1.0]hept-4-en-3-yl)-4-methyl-benzenesulfonamide

N-((1S,2R,3S,6R)-3-Methoxy-7-oxa-bicyclo[4.1.0]hept-4-en-2-yl)-4-methyl-benzenesulfonamide

DL-(1α,2β,3α,6β)-6-<(4-Methylphenylsulfonyl)amino>-4-cyclohexen-1,2,3-triol-3-acetat

DL-(1α,2β,3α,4α)-3-<(4-Methylphenylsulfonyl)amino>-5-cyclohexen-1,2,4-triol-4-acetat

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