4-methoxy-2-methylphenyl 3-deoxy-2,4-dimethoxy-3-phthalimido-α-D-xylo-hex-5-enopyranoside

Base Information

• Chemical Name: 4-methoxy-2-methylphenyl 3-deoxy-2,4-dimethoxy-3-phthalimido-α-D-xylo-hex-5-enopyranoside
• CAS No.: 108512-39-6
• Molecular Formula: C₂₄H₂₅NO₇
• Molecular Weight: 439.465
• Mol file: 108512-39-6.mol

Synonyms:4-methoxy-2-methylphenyl 3-deoxy-2,4-dimethoxy-3-phthalimido-α-D-xylo-hex-5-enopyranoside

Chemical Property of 4-methoxy-2-methylphenyl 3-deoxy-2,4-dimethoxy-3-phthalimido-α-D-xylo-hex-5-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methoxy-2-methylphenyl 3-deoxy-2,4-dimethoxy-3-phthalimido-α-D-xylo-hex-5-enopyranoside

There total 15 articles about 4-methoxy-2-methylphenyl 3-deoxy-2,4-dimethoxy-3-phthalimido-α-D-xylo-hex-5-enopyranoside 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: 58.0%

4-methoxy-2-methylphenyl 3,6-dideoxy-6-iodo-2,4-dimethoxy-3-phthalimido-α-D-glucopyranoside (108512-36-3) → 4-methoxy-2-methylphenyl 3-deoxy-2,4-dimethoxy-3-phthalimido-α-D-xylo-hex-5-enopyranoside (108512-39-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 50 ℃; for 60h;

DOI:10.1021/jo00392a013

Reference yield:

methyl 3-amino-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside (4603-89-8) → 4-methoxy-2-methylphenyl 3-deoxy-2,4-dimethoxy-3-phthalimido-α-D-xylo-hex-5-enopyranoside (108512-39-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 91 percent / triethylamine / dimethylsulfoxide / 16 h / 23 °C

2: 76 percent / Ag₂O / CH₂Cl₂ / 96 h / Heating

3: HOAc / 1 h / 100 °C

4: triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 15 h / 0 °C

5: 92 percent / conc. H₂SO₄ / acetic acid / 48 h / 23 °C

6: SnCl₄ / CH₂Cl₂ / 5 h / 23 °C

7: Dowex 2x8 / methanol / 0.5 h / Heating

8: 98 percent / pyridine / 48 h / 0 °C

9: 85 percent / Ag₂O / CH₂Cl₂ / 4 h / Heating

10: 100 percent / NaI / butan-2-one / 6 h / Heating

11: 58 percent / DBU / hexamethylphosphoric acid triamide / 60 h / 50 °C

With pyridine; dmap; Dowex 2x8; sulfuric acid; tin(IV) chloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; silver(l) oxide; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; butanone;

DOI:10.1021/jo00392a013

Reference yield:

N-ethoxycarbonylphthalimide (22509-74-6) → 4-methoxy-2-methylphenyl 3-deoxy-2,4-dimethoxy-3-phthalimido-α-D-xylo-hex-5-enopyranoside (108512-39-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 91 percent / triethylamine / dimethylsulfoxide / 16 h / 23 °C

2: 76 percent / Ag₂O / CH₂Cl₂ / 96 h / Heating

3: HOAc / 1 h / 100 °C

4: triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 15 h / 0 °C

5: 92 percent / conc. H₂SO₄ / acetic acid / 48 h / 23 °C

6: SnCl₄ / CH₂Cl₂ / 5 h / 23 °C

7: Dowex 2x8 / methanol / 0.5 h / Heating

8: 98 percent / pyridine / 48 h / 0 °C

9: 85 percent / Ag₂O / CH₂Cl₂ / 4 h / Heating

10: 100 percent / NaI / butan-2-one / 6 h / Heating

11: 58 percent / DBU / hexamethylphosphoric acid triamide / 60 h / 50 °C

With pyridine; dmap; Dowex 2x8; sulfuric acid; tin(IV) chloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; silver(l) oxide; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; butanone;

DOI:10.1021/jo00392a013

upstream raw materials:

4-methoxy-2-methylphenyl 3,6-dideoxy-6-iodo-2,4-dimethoxy-3-phthalimido-α-D-glucopyranoside

methyl 3-amino-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

N-ethoxycarbonylphthalimide

1-hydroxy-4-methoxy-2-methylbenzene

Downstream raw materials:

2-[(3S,4S,5R,6S)-2-Bromomethyl-2-(2,5-dioxo-pyrrolidin-1-yl)-3,5-dimethoxy-6-(4-methoxy-2-methyl-phenoxy)-tetrahydro-pyran-4-yl]-isoindole-1,3-dione

2-[(3S,4S,5R,6S)-2-[1-Iodo-meth-(E)-ylidene]-3,5-dimethoxy-6-(4-methoxy-2-methyl-phenoxy)-tetrahydro-pyran-4-yl]-isoindole-1,3-dione

Refernces