(1R,2S,4S,5S)-6-benzoyl-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

Base Information

Chemical Name:(1R,2S,4S,5S)-6-benzoyl-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one
CAS No.:127950-28-1
Molecular Formula:C₁₈H₂₁NO₆
Molecular Weight:347.368
Hs Code.:

Synonyms:(1R,2S,4S,5S)-6-benzoyl-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

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Chemical Property of (1R,2S,4S,5S)-6-benzoyl-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

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Technology Process of (1R,2S,4S,5S)-6-benzoyl-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

There total 11 articles about (1R,2S,4S,5S)-6-benzoyl-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-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: 92.0%

: 98-88-4
benzoyl chloride

: 127950-27-0
(1R,2S,4S,5S)-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

: 127950-28-1
(1R,2S,4S,5S)-6-benzoyl-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1246/bcsj.62.3950

Reference yield:

: (1R,3S,4S,5R,8R)-4-(2,4-dimethoxybenzylamino)-8-hydroxymethyl-3-methoxy-2,7-dioxabicyclo<3.3.0>octan-6-one

: 127950-28-1
(1R,2S,4S,5S)-6-benzoyl-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

Guidance literature:: Multi-step reaction with 4 steps

1: 67 percent / MeMgBr / tetrahydrofuran / 0.5 h

2: 92 percent / pyridinium p-toluenesulfonate / dimethylformamide / 18 h / Ambient temperature

3: 80 percent / K₂S₂O₈, K₂HPO₄ / H₂O; acetonitrile / 0.5 h / 78 °C

4: 92 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; dipotassium hydrogenphosphate; dipotassium peroxodisulfate; methylmagnesium bromide; triethylamine; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1246/bcsj.62.3950

Reference yield:

: 127950-24-7
(1R,2S,4S,5S)-2-<(1R)-1,2-dihydroxyethyl>-6-(2,4-dimethoxybenzyl)-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

: 127950-28-1
(1R,2S,4S,5S)-6-benzoyl-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / pyridinium p-toluenesulfonate / dimethylformamide / 18 h / Ambient temperature

2: 80 percent / K₂S₂O₈, K₂HPO₄ / H₂O; acetonitrile / 0.5 h / 78 °C

3: 92 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; dipotassium hydrogenphosphate; dipotassium peroxodisulfate; triethylamine; pyridinium p-toluenesulfonate; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1246/bcsj.62.3950