4-[(3S,5R)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose

Base Information

• Chemical Name: 4-[(3S,5R)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose
• CAS No.: 649571-99-3
• Molecular Formula: C₂₅H₂₉NO₆
• Molecular Weight: 439.508

Synonyms:4-[(3S,5R)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose

Chemical Property of 4-[(3S,5R)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose

Chemical Property:

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Technology Process of 4-[(3S,5R)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose

There total 3 articles about 4-[(3S,5R)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose 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: 83.0%

4-[(3R,5S)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose (649571-82-4) → 4-[(3S,5R)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose (649571-99-3)

Guidance literature:

With water; acetic acid; zinc; In tetrahydrofuran; at 60 ℃; for 5h;

DOI:10.1016/j.tetasy.2003.08.027

Reference yield: 36.0%

4-[(3R,5S)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose (649571-82-4) → (3S,5R)-5-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-3-hydroxy-2-oxopyrrolidine + 4-[(3S,5R)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose (649571-99-3)

Guidance literature:

With molybdenum hexacarbonyl; In water; acetonitrile; for 5h;

DOI:10.1016/j.tetasy.2007.08.001

Reference yield:

(Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-ylidene)amine N-oxide (162740-21-8,191997-36-1) → 4-[(3S,5R)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose (649571-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 19 percent / 0.5 h / 80 °C

2: 83 percent / glacial acetic acid; H₂O; Zn / tetrahydrofuran / 5 h / 60 °C

With water; acetic acid; zinc; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2003.08.027

upstream raw materials:

4-[(3R,5S)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose

(Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-ylidene)amine N-oxide

Downstream raw materials:

5,6,8-trideoxy-5,8-(N-benzylimino)-1,2-O-isopropylidene-3-O-benzyl-7(S)-hydroxy-α-D-glycero-D-gluco-octo-1,4-furanose

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