2,3-O-benzylidene-7-tert-butoxycarbonyl-2,3-exo-dihydroxy-7-azabicyclo[2.2.1]heptene

Base Information

Chemical Name:2,3-O-benzylidene-7-tert-butoxycarbonyl-2,3-exo-dihydroxy-7-azabicyclo[2.2.1]heptene
CAS No.:853086-51-8
Molecular Formula:C₁₈H₂₁NO₄
Molecular Weight:315.369
Hs Code.:

Synonyms:2,3-O-benzylidene-7-tert-butoxycarbonyl-2,3-exo-dihydroxy-7-azabicyclo[2.2.1]heptene

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Chemical Property of 2,3-O-benzylidene-7-tert-butoxycarbonyl-2,3-exo-dihydroxy-7-azabicyclo[2.2.1]heptene

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Technology Process of 2,3-O-benzylidene-7-tert-butoxycarbonyl-2,3-exo-dihydroxy-7-azabicyclo[2.2.1]heptene

There total 4 articles about 2,3-O-benzylidene-7-tert-butoxycarbonyl-2,3-exo-dihydroxy-7-azabicyclo[2.2.1]heptene 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:

: (+/-)-5,6-O-benzylidene-7-tert-butoxycarbonyl-5,6-exo-dihydroxy-2-(4-toluenesulfonyl)-7-azabicyclo[2.2.1]hept-2-ene

: 853086-51-8
2,3-O-benzylidene-7-tert-butoxycarbonyl-2,3-exo-dihydroxy-7-azabicyclo[2.2.1]heptene

Guidance literature:: (+/-)-5,6-O-benzylidene-7-tert-butoxycarbonyl-5,6-exo-dihydroxy-2-(4-toluenesulfonyl)-7-azabicyclo[2.2.1]hept-2-ene; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 3h; Heating;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Heating;
DOI:10.1039/b419154d

Reference yield:

: 5176-27-2
N-tert-butyloxycarbonyl-pyrrole

: 853086-51-8
2,3-O-benzylidene-7-tert-butoxycarbonyl-2,3-exo-dihydroxy-7-azabicyclo[2.2.1]heptene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 87 percent / 48 h / 85 °C

2.1: 70 percent / N-methylmorpholine-N-oxide; OsO₄; aq. NaHCO₃ / 2-methyl-propan-2-ol / 20 °C

3.1: 58 percent / TsOH*H₂O / 20 °C

4.1: AIBN; tributyltin hydride / benzene / 3 h / Heating

4.2: 75 mg / TBAF / tetrahydrofuran / Heating

With osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tert-butyl alcohol; benzene;
DOI:10.1039/b419154d

Reference yield:

: (+/-)-7-tert-butoxycarbonyl-5,6-exo-dihydroxy-2-(4-toluenesulfonyl)-7-azabicyclo[2.2.1]hept-2-ene

: 853086-51-8
2,3-O-benzylidene-7-tert-butoxycarbonyl-2,3-exo-dihydroxy-7-azabicyclo[2.2.1]heptene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 58 percent / TsOH*H₂O / 20 °C

2.1: AIBN; tributyltin hydride / benzene / 3 h / Heating

2.2: 75 mg / TBAF / tetrahydrofuran / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In benzene;
DOI:10.1039/b419154d