5,6-O-benzylidene-7-tert-butoxycarbonyl-2,3-di-O-trifluoromethanesulfonyl-2,3,5,6-exo-tetrahydroxy-7-azabicyclo[2.2.1]heptane

Base Information

Chemical Name:5,6-O-benzylidene-7-tert-butoxycarbonyl-2,3-di-O-trifluoromethanesulfonyl-2,3,5,6-exo-tetrahydroxy-7-azabicyclo[2.2.1]heptane
CAS No.:853086-55-2
Molecular Formula:C₂₀H₂₁F₆NO₁₀S₂
Molecular Weight:613.51
Hs Code.:

Synonyms:5,6-O-benzylidene-7-tert-butoxycarbonyl-2,3-di-O-trifluoromethanesulfonyl-2,3,5,6-exo-tetrahydroxy-7-azabicyclo[2.2.1]heptane

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Chemical Property of 5,6-O-benzylidene-7-tert-butoxycarbonyl-2,3-di-O-trifluoromethanesulfonyl-2,3,5,6-exo-tetrahydroxy-7-azabicyclo[2.2.1]heptane

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Technology Process of 5,6-O-benzylidene-7-tert-butoxycarbonyl-2,3-di-O-trifluoromethanesulfonyl-2,3,5,6-exo-tetrahydroxy-7-azabicyclo[2.2.1]heptane

There total 6 articles about 5,6-O-benzylidene-7-tert-butoxycarbonyl-2,3-di-O-trifluoromethanesulfonyl-2,3,5,6-exo-tetrahydroxy-7-azabicyclo[2.2.1]heptane 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: 81.0%

: 853086-53-0
2,3-O-benzylidene-7-tert-butoxycarbonyl-2,3,5,6-exo-tetrahydroxy-7-azabicyclo[2.2.1]heptane

: 358-23-6
trifluoromethylsulfonic anhydride

: 853086-55-2
5,6-O-benzylidene-7-tert-butoxycarbonyl-2,3-di-O-trifluoromethanesulfonyl-2,3,5,6-exo-tetrahydroxy-7-azabicyclo[2.2.1]heptane

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1039/b419154d

Reference yield:

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

: 853086-55-2
5,6-O-benzylidene-7-tert-butoxycarbonyl-2,3-di-O-trifluoromethanesulfonyl-2,3,5,6-exo-tetrahydroxy-7-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / N-methylmorpholine-N-oxide; OsO₄; aq. NaHCO₃ / tetrahydrofuran; 2-methyl-propan-2-ol / 20 °C

2: 81 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; osmium(VIII) oxide; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1039/b419154d

Reference yield:

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

: 853086-55-2
5,6-O-benzylidene-7-tert-butoxycarbonyl-2,3-di-O-trifluoromethanesulfonyl-2,3,5,6-exo-tetrahydroxy-7-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 75 mg / TBAF / tetrahydrofuran / Heating

2.1: 100 percent / N-methylmorpholine-N-oxide; OsO₄; aq. NaHCO₃ / tetrahydrofuran; 2-methyl-propan-2-ol / 20 °C

3.1: 81 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

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