tert-butyl (1S,2S,3R,4R)-7-benzyloxycarbonyl-2,3-dihydroxy-7-azabicyclo<2.2.1>heptane-1-carboxylate

Base Information

Chemical Name:tert-butyl (1S,2S,3R,4R)-7-benzyloxycarbonyl-2,3-dihydroxy-7-azabicyclo<2.2.1>heptane-1-carboxylate
CAS No.:221677-08-3
Molecular Formula:C₁₉H₂₅NO₆
Molecular Weight:363.411
Hs Code.:

Synonyms:tert-butyl (1S,2S,3R,4R)-7-benzyloxycarbonyl-2,3-dihydroxy-7-azabicyclo<2.2.1>heptane-1-carboxylate

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Chemical Property of tert-butyl (1S,2S,3R,4R)-7-benzyloxycarbonyl-2,3-dihydroxy-7-azabicyclo<2.2.1>heptane-1-carboxylate

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Technology Process of tert-butyl (1S,2S,3R,4R)-7-benzyloxycarbonyl-2,3-dihydroxy-7-azabicyclo<2.2.1>heptane-1-carboxylate

There total 1 articles about tert-butyl (1S,2S,3R,4R)-7-benzyloxycarbonyl-2,3-dihydroxy-7-azabicyclo<2.2.1>heptane-1-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: 88.0%

: 221677-07-2
tert-butyl 7-benzyloxycarbonyl-7-azabicyclo<2.2.1>-2-heptene-1-carboxylate

: 221677-08-3
tert-butyl (1S,2S,3R,4R)-7-benzyloxycarbonyl-2,3-dihydroxy-7-azabicyclo<2.2.1>heptane-1-carboxylate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; for 12h; Ambient temperature;
DOI:10.1021/jo982327c

Reference yield:

: 221677-08-3
tert-butyl (1S,2S,3R,4R)-7-benzyloxycarbonyl-2,3-dihydroxy-7-azabicyclo<2.2.1>heptane-1-carboxylate

: 221677-11-8
tert-butyl (1S,4R)-7-benzyloxycarbonyl-2-oxo-7-azabicyclo<2.2.1>heptane-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: imidazole / CH₂Cl₂ / 48 h / Ambient temperature

2: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 36 h / Ambient temperature

3: 72 percent / SmI₂ / tetrahydrofuran; methanol / 0.08 h / -78 °C

With 1H-imidazole; samarium diiodide; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo982327c

Reference yield:

: 221677-08-3
tert-butyl (1S,2S,3R,4R)-7-benzyloxycarbonyl-2,3-dihydroxy-7-azabicyclo<2.2.1>heptane-1-carboxylate

: tert-butyl (1S,4R)-7-benzyloxycarbonyl-2-Z-<(methoxycarbonyl)methylene>-7-azabicyclo<2.2.1>heptane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole / CH₂Cl₂ / 48 h / Ambient temperature

2: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 36 h / Ambient temperature

3: 72 percent / SmI₂ / tetrahydrofuran; methanol / 0.08 h / -78 °C

4: 5 percent / NaH / tetrahydrofuran / 72 h / Ambient temperature

With 1H-imidazole; samarium diiodide; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo982327c