(-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R,5R,6S)-5,6-dihydroxy-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Base Information

Chemical Name:(-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R,5R,6S)-5,6-dihydroxy-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
CAS No.:1333161-49-1
Molecular Formula:C₃₁H₄₁NO₄
Molecular Weight:491.671
Hs Code.:

Synonyms:(-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R,5R,6S)-5,6-dihydroxy-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

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Chemical Property of (-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R,5R,6S)-5,6-dihydroxy-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

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Technology Process of (-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R,5R,6S)-5,6-dihydroxy-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

There total 4 articles about (-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R,5R,6S)-5,6-dihydroxy-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-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: 79.0%

: 1333161-36-6
(-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

: 1333161-49-1
(-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R,5R,6S)-5,6-dihydroxy-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Guidance literature:: With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tet.2011.06.097

Reference yield:

: 65253-04-5
(-)-8-phenylmenthol

: 1333161-49-1
(-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R,5R,6S)-5,6-dihydroxy-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2.1: ozone / methanol; dichloromethane / 0.33 h / -78 °C

2.2: 12 h / Inert atmosphere

3.1: dichloromethane / 5 h / -78 °C / Inert atmosphere

4.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran; tert-butyl alcohol / 1 h / 20 °C / Inert atmosphere

With dmap; osmium(VIII) oxide; water; ozone; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 3.1: aza-Diels-Alder reaction;
DOI:10.1016/j.tet.2011.06.097

Reference yield:

: BF₃*C₂HF₃O₂*C₂₆H₃₃NO₂

: 1333161-49-1
(-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R,5R,6S)-5,6-dihydroxy-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: dichloromethane / 5 h / -78 °C / Inert atmosphere

2: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran; tert-butyl alcohol / 1 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 1: aza-Diels-Alder reaction;
DOI:10.1016/j.tet.2011.06.097