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

Base Information

Chemical Name:methyl 2-benzamido-2,3-dideoxy-5,6-O-isopropylidene-3-methoxycarbonyl-α-D-altrofuranoside
CAS No.:127950-29-2
Molecular Formula:C₁₉H₂₅NO₇
Molecular Weight:379.41
Hs Code.:

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

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

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Technology Process of methyl 2-benzamido-2,3-dideoxy-5,6-O-isopropylidene-3-methoxycarbonyl-α-D-altrofuranoside

There total 11 articles about methyl 2-benzamido-2,3-dideoxy-5,6-O-isopropylidene-3-methoxycarbonyl-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: 90.0%

: 67-56-1
methanol

: 127950-28-1
(1R,2S,4S,5S)-6-benzoyl-2-<(1R)-1,2-O-isopropylideneethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

: 127950-29-2
methyl 2-benzamido-2,3-dideoxy-5,6-O-isopropylidene-3-methoxycarbonyl-α-D-altrofuranoside

Guidance literature:: 1,8-diazabicyclo[5.4.0]undec-7-ene; for 0.5h; Heating;
DOI:10.1246/bcsj.62.3950

Reference yield:

: diethyl 2-malonate

: 127950-29-2
methyl 2-benzamido-2,3-dideoxy-5,6-O-isopropylidene-3-methoxycarbonyl-α-D-altrofuranoside

Guidance literature:: Multi-step reaction with 7 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

With dmap; sodium tetrahydroborate; dipotassium hydrogenphosphate; dipotassium peroxodisulfate; water; silica gel; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 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:

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 127950-29-2
methyl 2-benzamido-2,3-dideoxy-5,6-O-isopropylidene-3-methoxycarbonyl-α-D-altrofuranoside

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) 55percent NaH (in mineral oil), 2.) acetic acid / 1.) DMSO, 1.5 h, room temperature, 2.) DMSO, 20 h, room temperature

2: 45 percent / DCC / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 52 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Heating

4: 98 percent / silicagel powder, NaBH₄ / methanol / 0.25 h

5: 79 percent / H₂O, 1,8-diazabicyclo<5.4.0>undec-7-ene / pyridine / 0.75 h / Heating

6: 86 percent / Ag₂O / dimethylformamide / 4 h / Ambient temperature

7: 80 percent / K₂S₂O₈, K₂HPO₄ / H₂O; acetonitrile / 0.5 h / 78 °C

8: 92 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

9: 90 percent / DBU / 0.5 h / Heating

With dmap; sodium tetrahydroborate; dipotassium hydrogenphosphate; dipotassium peroxodisulfate; water; silica gel; sodium hydride; acetic acid; 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