(3S,5R)- and (3S,5S)-5-acetoxy-2-benzyl-3-[(4R)-2,2-dimethyl-3-(tert-butoxycarbonylamino)-1,3-oxazolidin-4-yl]isoxazolidine

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Chemical Name:(3S,5R)- and (3S,5S)-5-acetoxy-2-benzyl-3-[(4R)-2,2-dimethyl-3-(tert-butoxycarbonylamino)-1,3-oxazolidin-4-yl]isoxazolidine
CAS No.:298198-14-8
Molecular Formula:C₂₂H₃₂N₂O₆
Molecular Weight:420.506
Hs Code.:

Synonyms:(3S,5R)- and (3S,5S)-5-acetoxy-2-benzyl-3-[(4R)-2,2-dimethyl-3-(tert-butoxycarbonylamino)-1,3-oxazolidin-4-yl]isoxazolidine

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Chemical Property of (3S,5R)- and (3S,5S)-5-acetoxy-2-benzyl-3-[(4R)-2,2-dimethyl-3-(tert-butoxycarbonylamino)-1,3-oxazolidin-4-yl]isoxazolidine

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Technology Process of (3S,5R)- and (3S,5S)-5-acetoxy-2-benzyl-3-[(4R)-2,2-dimethyl-3-(tert-butoxycarbonylamino)-1,3-oxazolidin-4-yl]isoxazolidine

There total 8 articles about (3S,5R)- and (3S,5S)-5-acetoxy-2-benzyl-3-[(4R)-2,2-dimethyl-3-(tert-butoxycarbonylamino)-1,3-oxazolidin-4-yl]isoxazolidine 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:

: 108-24-7
acetic anhydride

: 1061738-40-6
(R)-4-((S)-2-Benzyl-5-hydroxy-isoxazolidin-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 298198-14-8
(3S,5R)- and (3S,5S)-5-acetoxy-2-benzyl-3-[(4R)-2,2-dimethyl-3-(tert-butoxycarbonylamino)-1,3-oxazolidin-4-yl]isoxazolidine

Guidance literature:: With pyridine; for 12h; Yield given; Ambient temperature;
DOI:10.1016/S0040-4039(98)01323-9

Reference yield:

: 158723-45-6,188965-45-9
(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]benzylamine N-oxide

: 298198-14-8
(3S,5R)- and (3S,5S)-5-acetoxy-2-benzyl-3-[(4R)-2,2-dimethyl-3-(tert-butoxycarbonylamino)-1,3-oxazolidin-4-yl]isoxazolidine

Guidance literature:: Multi-step reaction with 5 steps

1: 79 percent / CH₂Cl₂ / 2 h / -80 - -70 °C

2: 88 percent / HF-pyridine complex / tetrahydrofuran / 1 h / 0 °C

3: 95 percent / NaOMe / methanol / 2 h / 20 °C

4: DIBAH / CH₂Cl₂; toluene / 2 h / -80 °C

5: 0.492 g / pyridine / CH₂Cl₂ / 12 h / 20 °C

With pyridine; sodium methylate; diisobutylaluminium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Addition / 2: Substitution / 3: cyclocondensation / 4: Reduction / 5: Acetylation;
DOI:10.1021/jo0002689

Reference yield:

: 213752-98-8
methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate

: 298198-14-8
(3S,5R)- and (3S,5S)-5-acetoxy-2-benzyl-3-[(4R)-2,2-dimethyl-3-(tert-butoxycarbonylamino)-1,3-oxazolidin-4-yl]isoxazolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / NaOMe / methanol / 2 h / 20 °C

2: DIBAH / CH₂Cl₂; toluene / 2 h / -80 °C

3: 0.492 g / pyridine / CH₂Cl₂ / 12 h / 20 °C

With pyridine; sodium methylate; diisobutylaluminium hydride; In methanol; dichloromethane; toluene; 1: cyclocondensation / 2: Reduction / 3: Acetylation;
DOI:10.1021/jo0002689