(3aR,6R,6aS,1'R)-2-benzyl-6-(1',2'-dihydroxyethyl)-4-oxo-isoxazolidino[4,5-c]tetrahydrofuran

Base Information

Chemical Name:(3aR,6R,6aS,1'R)-2-benzyl-6-(1',2'-dihydroxyethyl)-4-oxo-isoxazolidino[4,5-c]tetrahydrofuran
CAS No.:929008-29-7
Molecular Formula:C₁₄H₁₇NO₅
Molecular Weight:279.293
Hs Code.:

Synonyms:(3aR,6R,6aS,1'R)-2-benzyl-6-(1',2'-dihydroxyethyl)-4-oxo-isoxazolidino[4,5-c]tetrahydrofuran

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Chemical Property of (3aR,6R,6aS,1'R)-2-benzyl-6-(1',2'-dihydroxyethyl)-4-oxo-isoxazolidino[4,5-c]tetrahydrofuran

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Technology Process of (3aR,6R,6aS,1'R)-2-benzyl-6-(1',2'-dihydroxyethyl)-4-oxo-isoxazolidino[4,5-c]tetrahydrofuran

There total 1 articles about (3aR,6R,6aS,1'R)-2-benzyl-6-(1',2'-dihydroxyethyl)-4-oxo-isoxazolidino[4,5-c]tetrahydrofuran 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: 95.0%

: (3aR,6R,7R,7aS)-7-acetoxy-6-acetoxymethyl-2-benzyl-4-oxo-tetrahydropyrano[3,4-d]isoxazolidine

: 929008-29-7
(3aR,6R,6aS,1'R)-2-benzyl-6-(1',2'-dihydroxyethyl)-4-oxo-isoxazolidino[4,5-c]tetrahydrofuran

Guidance literature:: With ammonia; In methanol; at 20 ℃; for 24h;
DOI:10.1080/07328300601039336

Reference yield:

: 929008-29-7
(3aR,6R,6aS,1'R)-2-benzyl-6-(1',2'-dihydroxyethyl)-4-oxo-isoxazolidino[4,5-c]tetrahydrofuran

: 929008-35-5
(3S,4S,5S)-N-benzyl-3,4-diacetoxy-5-(acetoxymethyl)piperidine

Guidance literature:: Multi-step reaction with 11 steps

1: sodium metaperiodate / methanol; H₂O / 1.5 h / 20 °C

2: 0.16 g / NaBH(OAc)3 / CH₂Cl₂

3: 73 percent / DMAP / CH₂Cl₂

4: LiAlH₄ / tetrahydrofuran / 0.5 h

5: 0.38 g / p-TsOH / 2 h / Heating

6: 90 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

7: Et₃N / CH₂Cl₂ / 1 h / 20 °C

8: acetic acid / methanol / 0.17 h / Heating

9: pyridine

10: H₂; K₂CO₃ / Pd/C / methanol / 24 h / 20 °C

11: 0.07 g / pyridine

With pyridine; dmap; sodium periodate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1080/07328300601039336

Reference yield:

: 929008-29-7
(3aR,6R,6aS,1'R)-2-benzyl-6-(1',2'-dihydroxyethyl)-4-oxo-isoxazolidino[4,5-c]tetrahydrofuran

: 215725-14-7
N-benzyl (-)-isofagomine

Guidance literature:: Multi-step reaction with 10 steps

1: sodium metaperiodate / methanol; H₂O / 1.5 h / 20 °C

2: 0.16 g / NaBH(OAc)3 / CH₂Cl₂

3: 73 percent / DMAP / CH₂Cl₂

4: LiAlH₄ / tetrahydrofuran / 0.5 h

5: 0.38 g / p-TsOH / 2 h / Heating

6: 90 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

7: Et₃N / CH₂Cl₂ / 1 h / 20 °C

8: acetic acid / methanol / 0.17 h / Heating

9: pyridine

10: H₂; K₂CO₃ / Pd/C / methanol / 24 h / 20 °C

With pyridine; dmap; sodium periodate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1080/07328300601039336