benzyl 5-hydroxy-2,2-dimethyl-7-oxohexahydro-3aH-4,8-epoxy[1,3]dioxolo[4',5':5,6]benzo[1,2-d]oxazole-3a-carboxylate

Base Information

Chemical Name:benzyl 5-hydroxy-2,2-dimethyl-7-oxohexahydro-3aH-4,8-epoxy[1,3]dioxolo[4',5':5,6]benzo[1,2-d]oxazole-3a-carboxylate
CAS No.:1301703-37-6
Molecular Formula:C₁₈H₁₉NO₈
Molecular Weight:377.351
Hs Code.:

Synonyms:benzyl 5-hydroxy-2,2-dimethyl-7-oxohexahydro-3aH-4,8-epoxy[1,3]dioxolo[4',5':5,6]benzo[1,2-d]oxazole-3a-carboxylate

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Chemical Property of benzyl 5-hydroxy-2,2-dimethyl-7-oxohexahydro-3aH-4,8-epoxy[1,3]dioxolo[4',5':5,6]benzo[1,2-d]oxazole-3a-carboxylate

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Technology Process of benzyl 5-hydroxy-2,2-dimethyl-7-oxohexahydro-3aH-4,8-epoxy[1,3]dioxolo[4',5':5,6]benzo[1,2-d]oxazole-3a-carboxylate

There total 4 articles about benzyl 5-hydroxy-2,2-dimethyl-7-oxohexahydro-3aH-4,8-epoxy[1,3]dioxolo[4',5':5,6]benzo[1,2-d]oxazole-3a-carboxylate 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: 39.0%

: 1301703-31-0
(3aR,4R,7S,7aR)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)-benzo[d][1,3]dioxole-3a,8-dicarboxylate

: 1301703-37-6
benzyl 5-hydroxy-2,2-dimethyl-7-oxohexahydro-3aH-4,8-epoxy[1,3]dioxolo[4',5':5,6]benzo[1,2-d]oxazole-3a-carboxylate

: 1301703-43-4
(3aR,4R,5R,6R,7S,7aR)-dibenzyl 5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-3a,8-dicarboxylate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1039/c1cc10643k

Reference yield:

: 1301703-27-4
(3aS,7aR)-benzyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate

: 1301703-37-6
benzyl 5-hydroxy-2,2-dimethyl-7-oxohexahydro-3aH-4,8-epoxy[1,3]dioxolo[4',5':5,6]benzo[1,2-d]oxazole-3a-carboxylate

: 1301703-43-4
(3aR,4R,5R,6R,7S,7aR)-dibenzyl 5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-3a,8-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutylammonium periodite / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere

2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; tetrabutylammonium periodite; 4-methylmorpholine N-oxide; In dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1039/c1cc10643k

Reference yield:

: 32359-20-9
(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid

: 1301703-37-6
benzyl 5-hydroxy-2,2-dimethyl-7-oxohexahydro-3aH-4,8-epoxy[1,3]dioxolo[4',5':5,6]benzo[1,2-d]oxazole-3a-carboxylate

: 1301703-43-4
(3aR,4R,5R,6R,7S,7aR)-dibenzyl 5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-3a,8-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / acetone

2: triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

3: tetrabutylammonium periodite / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere

4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; tetrabutylammonium periodite; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1039/c1cc10643k