(3aR,4R,5R,6R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate

Base Information

Chemical Name:(3aR,4R,5R,6R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate
CAS No.:1443540-32-6
Molecular Formula:C₂₄H₃₇NO₈Si
Molecular Weight:495.645
Hs Code.:

(3aR,4R,5R,6R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate

Synonyms:(3aR,4R,5R,6R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate

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Chemical Property of (3aR,4R,5R,6R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate

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Technology Process of (3aR,4R,5R,6R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate

There total 4 articles about (3aR,4R,5R,6R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-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: 81.0%

: 1443540-28-0
(3aR,4R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate

: 1443540-32-6
(3aR,4R,5R,6R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 48h;
DOI:10.1016/j.tet.2013.04.033

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 1443540-32-6
(3aR,4R,5R,6R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 1.08 h / 0 °C

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

3: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 48 h / 20 °C

With osmium(VIII) oxide; tetrabutylammonium periodite; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; water; acetone; tert-butyl alcohol; 2: |Diels-Alder Cycloaddition / 3: |Upjohn Dihydroxylation;
DOI:10.1016/j.tet.2013.04.033

Reference yield:

: 1379659-86-5
tert-butyl(((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methoxy)dimethylsilane

: 1443540-32-6
(3aR,4R,5R,6R,7S,7aR)-benzyl 3a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 48 h / 20 °C

With osmium(VIII) oxide; tetrabutylammonium periodite; 4-methylmorpholine N-oxide; In dichloromethane; water; acetone; tert-butyl alcohol; 1: |Diels-Alder Cycloaddition / 2: |Upjohn Dihydroxylation;
DOI:10.1016/j.tet.2013.04.033