2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

Base Information

• Chemical Name: 2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline
• CAS No.: 144152-57-8
• Molecular Formula: C₁₈H₂₁NO₆
• Molecular Weight: 347.368

Synonyms:2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

Chemical Property of 2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

There total 13 articles about 2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline 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:

(-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose (131940-20-0) → 2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ2'-oxazoline (144152-57-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 100 percent / 20percent aq. CH₃COOH / 5 h / 100 °C

2: 1.) Bu₂SnO, 2.) n-Bu₄NI / 1.) C₆H₆, reflux, 2 h, 2.) C₆H₆, reflux, 40 h

3: 98 percent / Dess-Martin periodinane, t-BuOH / CH₂Cl₂ / 2 h

4: 1.) NaH / 1.) THF, 0 deg C, 1 h, 2.) THF, -78 deg C, 1 h

5: 92 percent / L-selectride / tetrahydrofuran / 2 h

6: 68 percent / imidazole / dimethylformamide / 4 h

7: 70 percent / DBU

8: I(Coll)ClO₄ / acetonitrile / 1 h / 55 °C

9: Zn / ethanol / 4 h / Heating

10: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 3 min, 2.) CH₃OH, from -78 deg C to RT, 2 h

11: 72 percent / CH₂Cl₂; toluene; tetrahydrofuran / 1 h / -78 °C

12: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 deg C to 0 deg C, 2 h

With 1H-imidazole; oxalyl dichloride; dimethylsulfide; iodonium(di-γ-collidine) perchlorate; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; ozone; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; tert-butyl alcohol; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00068a025

Reference yield:

(-)-1,6-anhydro-4-O-benzoyl-β-D-mannopyranose (7225-53-8) → 2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ2'-oxazoline (144152-57-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) Bu₂SnO, 2.) n-Bu₄NI / 1.) C₆H₆, reflux, 2 h, 2.) C₆H₆, reflux, 40 h

2: 98 percent / Dess-Martin periodinane, t-BuOH / CH₂Cl₂ / 2 h

3: 1.) NaH / 1.) THF, 0 deg C, 1 h, 2.) THF, -78 deg C, 1 h

4: 92 percent / L-selectride / tetrahydrofuran / 2 h

5: 68 percent / imidazole / dimethylformamide / 4 h

6: 70 percent / DBU

7: I(Coll)ClO₄ / acetonitrile / 1 h / 55 °C

8: Zn / ethanol / 4 h / Heating

9: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 3 min, 2.) CH₃OH, from -78 deg C to RT, 2 h

10: 72 percent / CH₂Cl₂; toluene; tetrahydrofuran / 1 h / -78 °C

11: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 deg C to 0 deg C, 2 h

With 1H-imidazole; oxalyl dichloride; dimethylsulfide; iodonium(di-γ-collidine) perchlorate; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; tert-butyl alcohol; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00068a025

Reference yield:

1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose (14440-51-8) → 2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ2'-oxazoline (144152-57-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 97 percent / pyridine, DMAP / 1 h / 0 °C

2: 100 percent / 20percent aq. CH₃COOH / 5 h / 100 °C

3: 1.) Bu₂SnO, 2.) n-Bu₄NI / 1.) C₆H₆, reflux, 2 h, 2.) C₆H₆, reflux, 40 h

4: 98 percent / Dess-Martin periodinane, t-BuOH / CH₂Cl₂ / 2 h

5: 1.) NaH / 1.) THF, 0 deg C, 1 h, 2.) THF, -78 deg C, 1 h

6: 92 percent / L-selectride / tetrahydrofuran / 2 h

7: 68 percent / imidazole / dimethylformamide / 4 h

8: 70 percent / DBU

9: I(Coll)ClO₄ / acetonitrile / 1 h / 55 °C

10: Zn / ethanol / 4 h / Heating

11: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 3 min, 2.) CH₃OH, from -78 deg C to RT, 2 h

12: 72 percent / CH₂Cl₂; toluene; tetrahydrofuran / 1 h / -78 °C

13: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 deg C to 0 deg C, 2 h

With pyridine; 1H-imidazole; dmap; oxalyl dichloride; dimethylsulfide; iodonium(di-γ-collidine) perchlorate; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; ozone; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; tert-butyl alcohol; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00068a025

upstream raw materials:

(-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose

(-)-1,6-anhydro-4-O-benzoyl-β-D-mannopyranose

1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose

2'-methyl-(1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-3-C-vinyl-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

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