(1R,2S,3R,4S,5R)-benzyl 3,4-di-O-benzyl-5-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

Base Information

Chemical Name:(1R,2S,3R,4S,5R)-benzyl 3,4-di-O-benzyl-5-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS No.:1346167-15-4
Molecular Formula:C₂₉H₃₁NO₅
Molecular Weight:473.569
Hs Code.:

Synonyms:(1R,2S,3R,4S,5R)-benzyl 3,4-di-O-benzyl-5-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

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Chemical Property of (1R,2S,3R,4S,5R)-benzyl 3,4-di-O-benzyl-5-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

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Technology Process of (1R,2S,3R,4S,5R)-benzyl 3,4-di-O-benzyl-5-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

There total 5 articles about (1R,2S,3R,4S,5R)-benzyl 3,4-di-O-benzyl-5-hydroxy-8-azabicyclo[3.2.1]octane-2-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: 78.0%

: 1346167-14-3
(1S,2R,3S,7R)-benzyl 7-azido-2,3-di-O-benzyl-4-oxocycloheptanecarboxylate

: 1346167-15-4
(1R,2S,3R,4S,5R)-benzyl 3,4-di-O-benzyl-5-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:: With triphenylphosphine; In tetrahydrofuran; water; at 40 ℃; for 4h; Inert atmosphere;
DOI:10.1039/c1ob06038d

Reference yield:

: 1208102-25-3
(1R,2R,3R,4R,5R)-5-azido-1-benzoyloxy-2,3-dibenzyloxy-4-benzyloxymethyl-cycloheptane

: 1346167-15-4
(1R,2S,3R,4S,5R)-benzyl 3,4-di-O-benzyl-5-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: acetic acid; zinc(II) chloride / 3 h / 20 °C / Inert atmosphere

2: sodium methylate / methanol / 20 °C / Inert atmosphere

3: Jones reagent / water; acetone / 3 h / 0 °C / Inert atmosphere

4: caesium carbonate / acetonitrile / 0.25 h / 60 °C / Inert atmosphere

5: triphenylphosphine / tetrahydrofuran; water / 4 h / 40 °C / Inert atmosphere

With Jones reagent; sodium methylate; caesium carbonate; acetic acid; triphenylphosphine; zinc(II) chloride; In tetrahydrofuran; methanol; water; acetone; acetonitrile;
DOI:10.1039/c1ob06038d

Reference yield:

: 1346167-13-2
C₂₂H₂₃N₃O₅

: 1346167-15-4
(1R,2S,3R,4S,5R)-benzyl 3,4-di-O-benzyl-5-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: caesium carbonate / acetonitrile / 0.25 h / 60 °C / Inert atmosphere

2: triphenylphosphine / tetrahydrofuran; water / 4 h / 40 °C / Inert atmosphere

With caesium carbonate; triphenylphosphine; In tetrahydrofuran; water; acetonitrile;
DOI:10.1039/c1ob06038d