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

Base Information

Chemical Name:4-[(3S,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose
CAS No.:649571-79-9
Molecular Formula:C₂₀H₂₇NO₇
Molecular Weight:393.437
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 4-[(3S,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose

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Technology Process of 4-[(3S,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose

There total 1 articles about 4-[(3S,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-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: 34.0%

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: 162920-12-9,191997-35-0
(Z)-N-(5-deoxy-2,3-0-isopropylidene-l-O-methyl-D-yxo-l,4-furanose-5-ylidene)benzylamine N-oxide

: 649571-79-9
4-[(3S,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose

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

: 649571-77-7
4-[(3R,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose

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

Guidance literature:: at 80 ℃; for 0.5h;
DOI:10.1016/j.tetasy.2003.08.027

Reference yield: 78.0%

: 649571-79-9
4-[(3S,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose

: 649571-90-4
4-[(3R,5S)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose

Guidance literature:: With water; acetic acid; zinc; In tetrahydrofuran; at 60 ℃; for 5h;
DOI:10.1016/j.tetasy.2003.08.027

Reference yield:

: 649571-79-9
4-[(3S,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose

: 4-{(3R,5S)-1-benzyl-3-[(1S)-1-methoxy-1-phenyl-1-(trifluoromethyl)acetoxy]-2-oxo-5-pyrrolidinyl}-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / glacial acetic acid; H₂O; Zn / tetrahydrofuran / 5 h / 60 °C

2: 94 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

With dmap; water; acetic acid; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetasy.2003.08.027