8,10-dibenzyl-8,10-diaza-1-<1'-hydroxy-2',3'-O-isopropylidene>-5-(hydroxymethyl)-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione

Base Information

Chemical Name:8,10-dibenzyl-8,10-diaza-1-<1'-hydroxy-2',3'-O-isopropylidene>-5-(hydroxymethyl)-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione
CAS No.:92125-41-2
Molecular Formula:C₂₉H₃₆N₂O₈
Molecular Weight:540.613
Hs Code.:

Synonyms:8,10-dibenzyl-8,10-diaza-1-<1'-hydroxy-2',3'-O-isopropylidene>-5-(hydroxymethyl)-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione

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Chemical Property of 8,10-dibenzyl-8,10-diaza-1-<1'-hydroxy-2',3'-O-isopropylidene>-5-(hydroxymethyl)-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione

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Technology Process of 8,10-dibenzyl-8,10-diaza-1-<1'-hydroxy-2',3'-O-isopropylidene>-5-(hydroxymethyl)-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione

There total 13 articles about 8,10-dibenzyl-8,10-diaza-1-<1'-hydroxy-2',3'-O-isopropylidene>-5-(hydroxymethyl)-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione 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: 71.0%

: 92125-40-1
8,10-dibenzyl-8,10-diaza-1-<1'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene>-5-<((tert-butyldimethylsilyl)oxy)methyl>-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione

: 92125-41-2
8,10-dibenzyl-8,10-diaza-1-<1'-hydroxy-2',3'-O-isopropylidene>-5-(hydroxymethyl)-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;
DOI:10.1021/ja00297a035

Reference yield:

: 92098-02-7
1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione

: 92125-41-2
8,10-dibenzyl-8,10-diaza-1-<1'-hydroxy-2',3'-O-isopropylidene>-5-(hydroxymethyl)-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 13.5 percent / (dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 91 percent / silver triflate / tetrahydrofuran / 0.33 h / Ambient temperature

3: 1.) LDA / 1.) THF, -100 deg C, 5 min; 2.) -100 deg C, 2 min

4: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

5: 1.) tert-butyllithium; 2.) O₂ / 1.) THF, -100 deg C, 2 min; 2.) THF, -100 deg C, 10 min

6: 71 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; tetrabutyl ammonium fluoride; tert.-butyl lithium; oxygen; silver trifluoromethanesulfonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00297a035

Reference yield:

: 92098-01-6
1,4-dimethyl-3-(2'-thiopyridyl)-6-(2''-δ-valerolactonyl)-2,5-piperazinedione (syn, major diastereomer)

: 92125-41-2
8,10-dibenzyl-8,10-diaza-1-<1'-hydroxy-2',3'-O-isopropylidene>-5-(hydroxymethyl)-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 54 percent / lithium aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C

2: 13.5 percent / (dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 91 percent / silver triflate / tetrahydrofuran / 0.33 h / Ambient temperature

4: 1.) LDA / 1.) THF, -100 deg C, 5 min; 2.) -100 deg C, 2 min

5: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

6: 1.) tert-butyllithium; 2.) O₂ / 1.) THF, -100 deg C, 2 min; 2.) THF, -100 deg C, 10 min

7: 71 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tert.-butyl lithium; oxygen; silver trifluoromethanesulfonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00297a035