ethyl [(1R,2R,3S,4R,5S)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-{N¹-butyl-N³-(4-fluorophenyl)-1-ureidyl}-1,4-heptofuranos-5-yl]uronoate

Base Information

• Chemical Name: ethyl [(1R,2R,3S,4R,5S)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-{N¹-butyl-N³-(4-fluorophenyl)-1-ureidyl}-1,4-heptofuranos-5-yl]uronoate
• CAS No.: 623559-55-7
• Molecular Formula: C₃₀H₃₉FN₂O₇
• Molecular Weight: 558.647

Synonyms:ethyl [(1R,2R,3S,4R,5S)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-{N¹-butyl-N³-(4-fluorophenyl)-1-ureidyl}-1,4-heptofuranos-5-yl]uronoate

Chemical Property of ethyl [(1R,2R,3S,4R,5S)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-{N¹-butyl-N³-(4-fluorophenyl)-1-ureidyl}-1,4-heptofuranos-5-yl]uronoate

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Technology Process of ethyl [(1R,2R,3S,4R,5S)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-{N¹-butyl-N³-(4-fluorophenyl)-1-ureidyl}-1,4-heptofuranos-5-yl]uronoate

There total 2 articles about ethyl [(1R,2R,3S,4R,5S)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-{N¹-butyl-N³-(4-fluorophenyl)-1-ureidyl}-1,4-heptofuranos-5-yl]uronoate 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: 85.0%

para-fluorophenyl isocyanate (1195-45-5) + (1R,2R,3S,4R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-α-D-gluco-heptofuranuronate (500908-12-3) → ethyl [(1R,2R,3S,4R,5S)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-{N1-butyl-N3-(4-fluorophenyl)-1-ureidyl}-1,4-heptofuranos-5-yl]uronoate (623559-55-7)

Guidance literature:

In dichloromethane; at 30 ℃; for 4h;

DOI:10.1016/S0968-0896(03)00214-1

Reference yield:

ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-48-3) → ethyl [(1R,2R,3S,4R,5S)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-{N1-butyl-N3-(4-fluorophenyl)-1-ureidyl}-1,4-heptofuranos-5-yl]uronoate (623559-55-7)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol

2: 85 percent / CH₂Cl₂ / 4 h / 30 °C

In ethanol; dichloromethane;

DOI:10.1016/S0968-0896(03)00214-1

Reference yield:

ethyl [(1R,2R,3S,4R,5S)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-{N1-butyl-N3-(4-fluorophenyl)-1-ureidyl}-1,4-heptofuranos-5-yl]uronoate (623559-55-7) → (1'R,2'R,3'S,4'R,6S)-N1-butyl-N3-(4-fluorophenyl)-5,6-dihydro-(1',2'-O-isopropylidene-3'-O-benzyl-1',2',3',4'-tetrahydrofuranos-4'-yl)pyrimidin-2,4-dione

Guidance literature:

With 4 A molecular sieve; tetrabutylammomium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 2.5h; Heating;

DOI:10.1016/S0968-0896(03)00214-1

upstream raw materials:

para-fluorophenyl isocyanate

(1R,2R,3S,4R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-α-D-gluco-heptofuranuronate

ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

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