4-exo-acetoxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

Base Information

Chemical Name:4-exo-acetoxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)
CAS No.:116233-64-8
Molecular Formula:C₁₈H₂₃NO₆
Molecular Weight:349.384
Hs Code.:

Synonyms:4-exo-acetoxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

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Chemical Property of 4-exo-acetoxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

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Technology Process of 4-exo-acetoxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

There total 16 articles about 4-exo-acetoxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D) 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: 99.0%

: 108-24-7
acetic anhydride

: 116233-63-7
4-exo-hydroxy-3-endo-methoxy-6-<((R)-1-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

: 116233-64-8
4-exo-acetoxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 23 ℃; for 3h;
DOI:10.1021/jo00255a020

Reference yield:

: 108-24-7
acetic anhydride

: 116233-63-7
4-exo-hydroxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (L)

: 116233-64-8
4-exo-acetoxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (L)

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 23 ℃; for 3h;
DOI:10.1021/jo00255a020

Reference yield:

: 116233-54-6
3,6-dihydro-2H-pyran-2-carboxylic acid

: 116233-64-8
4-exo-acetoxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (L)

Guidance literature:: Multi-step reaction with 7 steps

1: oxalyl chloride / toluene / 0.5 h

2: Et₃N / toluene / 23 °C

3: pentane / 1 h

4: Br(coll)2ClO₄ (bromonium bis(collidine) perchlorate) / CH₂Cl₂ / 1.) 5 min. -78 deg C; 2.) from -78 deg C to RT

5: 100 mg / potassium tert-butoxide / dimethylsulfoxide / 12 h / 23 °C

6: m-chloroperbenzoic acid (mCPBA) / 12 h / 23 °C

7: 4-(N,N-dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 3 h / 23 °C

With dmap; oxalyl dichloride; bromonium bis(collidine) perchlorate; potassium tert-butylate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; dimethyl sulfoxide; toluene; pentane;
DOI:10.1021/jo00255a020