Acetic acid (2R,3S,4R,5S)-4,5-diacetoxy-1-(4-methoxy-phenyl)-6-oxo-2-propa-1,2-dienyl-piperidin-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4R,5S)-4,5-diacetoxy-1-(4-methoxy-phenyl)-6-oxo-2-propa-1,2-dienyl-piperidin-3-yl ester
CAS No.:223608-69-3
Molecular Formula:C₂₁H₂₃NO₈
Molecular Weight:417.416
Hs Code.:

Synonyms:Acetic acid (2R,3S,4R,5S)-4,5-diacetoxy-1-(4-methoxy-phenyl)-6-oxo-2-propa-1,2-dienyl-piperidin-3-yl ester

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Chemical Property of Acetic acid (2R,3S,4R,5S)-4,5-diacetoxy-1-(4-methoxy-phenyl)-6-oxo-2-propa-1,2-dienyl-piperidin-3-yl ester

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Technology Process of Acetic acid (2R,3S,4R,5S)-4,5-diacetoxy-1-(4-methoxy-phenyl)-6-oxo-2-propa-1,2-dienyl-piperidin-3-yl ester

There total 5 articles about Acetic acid (2R,3S,4R,5S)-4,5-diacetoxy-1-(4-methoxy-phenyl)-6-oxo-2-propa-1,2-dienyl-piperidin-3-yl ester 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%

: 13361-64-3
trimethyl(propargyl)silane

: 223608-68-2
Acetic acid (3R,4R,5S)-3,4,5-triacetoxy-1-(4-methoxy-phenyl)-6-oxo-piperidin-2-yl ester

: 223608-69-3
Acetic acid (2R,3S,4R,5S)-4,5-diacetoxy-1-(4-methoxy-phenyl)-6-oxo-2-propa-1,2-dienyl-piperidin-3-yl ester

Guidance literature:: With boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; In acetonitrile;
DOI:10.1016/S0957-4166(99)00030-0

Reference yield:

: 63181-58-8
(2R,3s,4S)-2,3,4-triacetoxyglutaric anhydride

: 223608-69-3
Acetic acid (2R,3S,4R,5S)-4,5-diacetoxy-1-(4-methoxy-phenyl)-6-oxo-2-propa-1,2-dienyl-piperidin-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 2.) DCC, HOBT / 1.) acetone, RT, 2 h, 2.) CH₂Cl₂, reflux, 6 h

2: (1R,2S)-1-phenyl-2-piperidino-1-propanethiol, Et₂Zn, bis(2,6-dimethylphenoxy)borane / toluene / 16 h / -10 °C

3: 87 percent / pyridine / CH₂Cl₂ / Ambient temperature

4: 88 percent / BF₃*Et₂O, tert-butyldimethylsilyl triflate / acetonitrile

With pyridine; bis(2,6-dimethylphenoxy)borane; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; diethylzinc; benzotriazol-1-ol; dicyclohexyl-carbodiimide; (1R,2S)-(-)-1-phenyl-2-piperidinopropane-1-thiol; In dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0957-4166(99)00030-0

Reference yield:

: 104-94-9
4-methoxy-aniline

: 223608-69-3
Acetic acid (2R,3S,4R,5S)-4,5-diacetoxy-1-(4-methoxy-phenyl)-6-oxo-2-propa-1,2-dienyl-piperidin-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 2.) DCC, HOBT / 1.) acetone, RT, 2 h, 2.) CH₂Cl₂, reflux, 6 h

2: (1R,2S)-1-phenyl-2-piperidino-1-propanethiol, Et₂Zn, bis(2,6-dimethylphenoxy)borane / toluene / 16 h / -10 °C

3: 87 percent / pyridine / CH₂Cl₂ / Ambient temperature

4: 88 percent / BF₃*Et₂O, tert-butyldimethylsilyl triflate / acetonitrile

With pyridine; bis(2,6-dimethylphenoxy)borane; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; diethylzinc; benzotriazol-1-ol; dicyclohexyl-carbodiimide; (1R,2S)-(-)-1-phenyl-2-piperidinopropane-1-thiol; In dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0957-4166(99)00030-0