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

Base Information

• Chemical Name: 4-methoxy-2-methylphenyl 3,6-dideoxy-6-iodo-2,4-dimethoxy-3-phthalimido-α-D-glucopyranoside
• CAS No.: 108512-36-3
• Molecular Formula: C₂₄H₂₆INO₇
• Molecular Weight: 567.377

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

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

Chemical Property:

Purity/Quality:

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

There total 14 articles about 4-methoxy-2-methylphenyl 3,6-dideoxy-6-iodo-2,4-dimethoxy-3-phthalimido-α-D-glucopyranoside 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: 100.0%

4-methoxy-2-methylphenyl 3-deoxy-6-<(methylsulfonyl)oxy>-2,4-dimethoxy-3-phthalimido-α-D-glucopyranoside (108512-35-2) → 4-methoxy-2-methylphenyl 3,6-dideoxy-6-iodo-2,4-dimethoxy-3-phthalimido-α-D-glucopyranoside (108512-36-3)

Guidance literature:

With sodium iodide; In butanone; for 6h; Heating;

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 3,6-dideoxy-6-iodo-2,4-dimethoxy-3-phthalimido-α-D-glucopyranoside (108512-36-3)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; dmap; Dowex 2x8; sulfuric acid; tin(IV) chloride; acetic acid; triethylamine; sodium iodide; silver(l) oxide; In methanol; 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 3,6-dideoxy-6-iodo-2,4-dimethoxy-3-phthalimido-α-D-glucopyranoside (108512-36-3)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; dmap; Dowex 2x8; sulfuric acid; tin(IV) chloride; acetic acid; triethylamine; sodium iodide; silver(l) oxide; In methanol; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; butanone;

DOI:10.1021/jo00392a013

upstream raw materials:

4-methoxy-2-methylphenyl 3-deoxy-6-<(methylsulfonyl)oxy>-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

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

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