(3aS,4S,4aR,7aR,8R,8aS)-7a-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylhexahydro-4,8-(epoxyimino)benzo[1,2-d:4,5-d']bis([1,3]dioxole)-2-one

Base Information

• Chemical Name: (3aS,4S,4aR,7aR,8R,8aS)-7a-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylhexahydro-4,8-(epoxyimino)benzo[1,2-d:4,5-d']bis([1,3]dioxole)-2-one
• CAS No.: 1454691-32-7
• Molecular Formula: C₁₇H₂₉NO₇Si
• Molecular Weight: 387.505
• Mol file: 1454691-32-7.mol

Synonyms:

Chemical Property of (3aS,4S,4aR,7aR,8R,8aS)-7a-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylhexahydro-4,8-(epoxyimino)benzo[1,2-d:4,5-d']bis([1,3]dioxole)-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,4aR,7aR,8R,8aS)-7a-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylhexahydro-4,8-(epoxyimino)benzo[1,2-d:4,5-d']bis([1,3]dioxole)-2-one

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

t-butyldimethylsiyl triflate (69739-34-0) → (3aR,4S,5S,6S,7R,7aR)-benzyl 7a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate (1443540-34-8) + (3aS,4S,4aR,7aR,8R,8aS)-7a-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylhexahydro-4,8-(epoxyimino)benzo[1,2-d:4,5-d']bis([1,3]dioxole)-2-one (1454691-32-7)

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:

((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methanol (172877-76-8) → (3aR,4S,5S,6S,7R,7aR)-benzyl 7a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate (1443540-34-8) + (3aS,4S,4aR,7aR,8R,8aS)-7a-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylhexahydro-4,8-(epoxyimino)benzo[1,2-d:4,5-d']bis([1,3]dioxole)-2-one (1454691-32-7)

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:

tert-butyl(((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methoxy)dimethylsilane (1379659-86-5) → (3aR,4S,5S,6S,7R,7aR)-benzyl 7a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate (1443540-34-8) + (3aS,4S,4aR,7aR,8R,8aS)-7a-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylhexahydro-4,8-(epoxyimino)benzo[1,2-d:4,5-d']bis([1,3]dioxole)-2-one (1454691-32-7)

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

upstream raw materials:

t-butyldimethylsiyl triflate

((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methanol

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