1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}thymine

Base Information

Chemical Name:1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}thymine
CAS No.:298198-31-9
Molecular Formula:C₂₂H₃₀N₄O₆
Molecular Weight:446.503
Hs Code.:

Synonyms:1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}thymine

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Chemical Property of 1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}thymine

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Technology Process of 1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}thymine

There total 10 articles about 1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}thymine 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: 82.0%

: 213753-05-0
1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2,2-dimethyl-1,3-oxazolidin-4-yl]isoxazolidin-5-yl}thymine

: 298198-31-9
1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}thymine

Guidance literature:: With acetic acid; at 60 ℃; for 2h;
DOI:10.1021/jo0002689

Reference yield:

: 29601-98-7
N-benzylhydroxylamine hydrochloride

: 298198-31-9
1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}thymine

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / tetrahydrofuran / 12 h / 20 °C

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

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

4: 0.492 g / pyridine / CH₂Cl₂ / 12 h / 20 °C

5: 33 percent / TMSOTf / acetonitrile / 12 h / 20 °C

6: 82 percent / aq. AcOH / 2 h / 60 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; sodium methylate; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 1: Michael addition / 2: cyclocondensation / 3: Reduction / 4: Acetylation / 5: Condensation / 6: Hydrolysis;
DOI:10.1021/jo0002689

Reference yield:

: 123751-10-0
N-(tert-butoxycarbonyl)-2,2-dimethyl-4(R)-<2'-carboxymethylethenyl>-oxazolidine

: 298198-31-9
1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}thymine

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / tetrahydrofuran / 12 h / 20 °C

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

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

4: 0.492 g / pyridine / CH₂Cl₂ / 12 h / 20 °C

5: 33 percent / TMSOTf / acetonitrile / 12 h / 20 °C

6: 82 percent / aq. AcOH / 2 h / 60 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; sodium methylate; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 1: Michael addition / 2: cyclocondensation / 3: Reduction / 4: Acetylation / 5: Condensation / 6: Hydrolysis;
DOI:10.1021/jo0002689