4-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one

Base Information

• Chemical Name: 4-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one
• CAS No.: 148236-83-3
• Molecular Formula: C₂₆H₂₉NO₇
• Molecular Weight: 467.519

Synonyms:4-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one

Chemical Property of 4-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one

There total 6 articles about 4-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one 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: 76.0%

4-Methoxyphenyl isocyanate (5416-93-3) + (3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-vinyl-oxiranyl)-tetrahydro-furo[2,3-d][1,3]dioxole (148236-81-1) → 4-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one (148236-83-3)

Guidance literature:

With triisopropyl phosphite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1016/0040-4039(93)85033-S

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → 4-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one (148236-83-3)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 4 h / Ambient temperature

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / -78 deg C, 2 h

3: 80 percent / tetrahydrofuran / 1 h / Ambient temperature

4: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

5: PPh₃, diethyl azodicarboxylate / toluene / 5 h / Heating

6: 76 percent / triisopropyl phosphite / Pd(PPh)3 / tetrahydrofuran / 18 h / Ambient temperature

With 1H-imidazole; oxalyl dichloride; triisopropyl phosphite; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0040-4039(93)85033-S

Reference yield:

1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol (106445-04-9) → 4-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one (148236-83-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / -78 deg C, 2 h

2: 80 percent / tetrahydrofuran / 1 h / Ambient temperature

3: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: PPh₃, diethyl azodicarboxylate / toluene / 5 h / Heating

5: 76 percent / triisopropyl phosphite / Pd(PPh)3 / tetrahydrofuran / 18 h / Ambient temperature

With oxalyl dichloride; triisopropyl phosphite; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; toluene;

DOI:10.1016/0040-4039(93)85033-S

upstream raw materials:

4-Methoxyphenyl isocyanate

(3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-vinyl-oxiranyl)-tetrahydro-furo[2,3-d][1,3]dioxole

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol

Downstream raw materials:

(R)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-benzyloxymethyl-3-(4-methoxy-phenyl)-oxazolidin-2-one

5-benzamido-5-C-(hydroxymethyl)-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone

(R)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-benzyloxymethyl-oxazolidin-2-one

Benzoic acid (3aR,3bS,6S,6aR,7aR)-6-benzoylamino-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-ylmethyl ester

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