(1α,2α,3α,4α,7α,8α)-(+/-)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.0^2,4>oct-5-en-5-ol-benzolsulfonat

Base Information

• Chemical Name: (1α,2α,3α,4α,7α,8α)-(+/-)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.0^2,4>oct-5-en-5-ol-benzolsulfonat
• CAS No.: 109583-95-1
• Molecular Formula: C₂₆H₂₂O₇S₃
• Molecular Weight: 542.654

Synonyms:(1α,2α,3α,4α,7α,8α)-(+/-)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.0^2,4>oct-5-en-5-ol-benzolsulfonat

Chemical Property of (1α,2α,3α,4α,7α,8α)-(+/-)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.0^2,4>oct-5-en-5-ol-benzolsulfonat

Chemical Property:

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• Pictogram(s):  
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Technology Process of (1α,2α,3α,4α,7α,8α)-(+/-)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.0^2,4>oct-5-en-5-ol-benzolsulfonat

There total 7 articles about (1α,2α,3α,4α,7α,8α)-(+/-)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.0^2,4>oct-5-en-5-ol-benzolsulfonat 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: 36.0%

(1α,2α,3α,4α,5α,6α,7α,8α)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.02,4>octan-5,6-diol-bis(benzolsulfonat) (96362-82-2) → (+/-)-cis-5,8-Bis(phenylsulfonyl)cycloocta-1,3,6-trien-2-ol-benzolsulfonat (109531-80-8) + (1α,2α,3α,4α,7α,8α)-(+/-)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.02,4>oct-5-en-5-ol-benzolsulfonat (109583-95-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -50 ℃; for 1h;

DOI:10.1016/S0040-4039(00)84314-2

Reference yield:

methylphenylsulfonate (3112-85-4) → (1α,2α,3α,4α,7α,8α)-(+/-)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.02,4>oct-5-en-5-ol-benzolsulfonat (109583-95-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) 2,3M n-BuLi / 1) hexane, THF, 0 deg C, 20 h, 2) 12 h, 20 deg C

2: 94 percent / p-ToOH / 1 h / Heating

3: 88 percent / NEt₃ / CH₂Cl₂ / 0.5 h / 20 °C

4: 85 percent / 2.0M n-BuLi, diisopropylamine / hexane; tetrahydrofuran / 0.08 h / -20 °C

5: 91 percent / conc. HCl / methanol / 0.17 h / Heating

6: 91 percent / NEt₃, 4-(dimethylamino)pyridine / CH₂Cl₂; pyridine / 12 h

7: KOtBu / tetrahydrofuran / 1 h / -50 °C

With hydrogenchloride; dmap; n-butyllithium; potassium tert-butylate; toluene-4-sulfonic acid; triethylamine; diisopropylamine; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane;

Reference yield:

(1α,2α,3α,4α,5α,6α,7α,8α)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.02,4>octan-5,6-diol (96362-80-0) → (1α,2α,3α,4α,7α,8α)-(+/-)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.02,4>oct-5-en-5-ol-benzolsulfonat (109583-95-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NEt₃, 4-(dimethylamino)pyridine / CH₂Cl₂; pyridine / 12 h

2: KOtBu / tetrahydrofuran / 1 h / -50 °C

With dmap; potassium tert-butylate; triethylamine; In tetrahydrofuran; pyridine; dichloromethane;

upstream raw materials:

(1α,2α,3α,4α,5α,6α,7α,8α)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.0^2,4>octan-5,6-diol-bis(benzolsulfonat)

methylphenylsulfonate

(1α,2α,3α,4α,5α,6α,7α,8α)-3,8-Bis(phenylsulfonyl)tricyclo<5.1.0.0^2,4>octan-5,6-diol

(1α,2α,3α,4β,5α,6α,7α)-(+/-)-2,3-O-Isopropyliden-7-(phenylsulfonyl)-4-(phenylsulfonylmethyl)bicyclo<4.1.o>heptan-2,3,5-triol

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