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

Base Information

Chemical Name:1-{(3S,5R)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}uracil
CAS No.:298198-32-0
Molecular Formula:C₂₁H₂₈N₄O₆
Molecular Weight:432.477
Hs Code.:

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

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

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

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

: 298198-24-0
1-{(3S,5R)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2,2-dimethyl-1,3-oxazolidin-4-yl]isoxazolidin-5-yl}uracil

: 298198-32-0
1-{(3S,5R)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}uracil

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

Reference yield:

: 29601-98-7
N-benzylhydroxylamine hydrochloride

: 298198-32-0
1-{(3S,5R)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}uracil

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: 36 percent / TMSOTf / acetonitrile / 12 h / 20 °C

6: 88 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

: 298198-32-0
1-{(3S,5R)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}uracil

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: 36 percent / TMSOTf / acetonitrile / 12 h / 20 °C

6: 88 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