methyl 2-benzamido-3-(3-chlorobenzoyldioxycarbonyl)-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside

Base Information

• Chemical Name: methyl 2-benzamido-3-(3-chlorobenzoyldioxycarbonyl)-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside
• CAS No.: 127950-31-6
• Molecular Formula: C₂₅H₂₆ClNO₉
• Molecular Weight: 519.936

Synonyms:methyl 2-benzamido-3-(3-chlorobenzoyldioxycarbonyl)-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside

Chemical Property of methyl 2-benzamido-3-(3-chlorobenzoyldioxycarbonyl)-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of methyl 2-benzamido-3-(3-chlorobenzoyldioxycarbonyl)-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside

There total 13 articles about methyl 2-benzamido-3-(3-chlorobenzoyldioxycarbonyl)-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside 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: 84.0%

3-chloro-benzenecarboperoxoic acid (937-14-4) + methyl 2-benzamido-3-carboxy-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside (127950-30-5) → methyl 2-benzamido-3-(3-chlorobenzoyldioxycarbonyl)-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside (127950-31-6)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; for 0.25h; Ambient temperature;

DOI:10.1246/bcsj.62.3950

Reference yield:

diethyl 2-malonate → methyl 2-benzamido-3-(3-chlorobenzoyldioxycarbonyl)-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside (127950-31-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 52 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Heating

2: 98 percent / silicagel powder, NaBH₄ / methanol / 0.25 h

3: 79 percent / H₂O, 1,8-diazabicyclo<5.4.0>undec-7-ene / pyridine / 0.75 h / Heating

4: 86 percent / Ag₂O / dimethylformamide / 4 h / Ambient temperature

5: 80 percent / K₂S₂O₈, K₂HPO₄ / H₂O; acetonitrile / 0.5 h / 78 °C

6: 92 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

7: 90 percent / DBU / 0.5 h / Heating

8: 99 percent / 1M NaOH / methanol; H₂O / 0.5 h / Heating

9: 84 percent / DCC / CH₂Cl₂ / 0.25 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; dipotassium hydrogenphosphate; dipotassium peroxodisulfate; water; silica gel; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; silver(l) oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1246/bcsj.62.3950

Reference yield:

(2S,3R,4R)-2,3-epoxy-4,5-isopropylidenedioxypentanoic acid → methyl 2-benzamido-3-(3-chlorobenzoyldioxycarbonyl)-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside (127950-31-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 45 percent / DCC / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 52 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Heating

3: 98 percent / silicagel powder, NaBH₄ / methanol / 0.25 h

4: 79 percent / H₂O, 1,8-diazabicyclo<5.4.0>undec-7-ene / pyridine / 0.75 h / Heating

5: 86 percent / Ag₂O / dimethylformamide / 4 h / Ambient temperature

6: 80 percent / K₂S₂O₈, K₂HPO₄ / H₂O; acetonitrile / 0.5 h / 78 °C

7: 92 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

8: 90 percent / DBU / 0.5 h / Heating

9: 99 percent / 1M NaOH / methanol; H₂O / 0.5 h / Heating

10: 84 percent / DCC / CH₂Cl₂ / 0.25 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; dipotassium hydrogenphosphate; dipotassium peroxodisulfate; water; silica gel; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; silver(l) oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1246/bcsj.62.3950

upstream raw materials:

3-chloro-benzenecarboperoxoic acid

methyl 2-benzamido-3-carboxy-2,3-dideoxy-5,6-O-isopropylidene-α-D-altrofuranoside

(1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

(1R,2S,4RS,5R)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropylidenedioxyethyl>-3-oxa-7-oxo-6-azabicyclo<3.2.0>heptane-5-carboxylate

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