p-methoxyphenyl O-[3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-levulinoyl-β-D-glucopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside

Base Information

• Chemical Name: p-methoxyphenyl O-[3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-levulinoyl-β-D-glucopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside
• CAS No.: 202864-98-0
• Molecular Formula: C₆₈H₆₀Cl₄N₂O₁₆
• Molecular Weight: 1303.04

Synonyms:p-methoxyphenyl O-[3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-levulinoyl-β-D-glucopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside

Chemical Property of p-methoxyphenyl O-[3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-levulinoyl-β-D-glucopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside

Chemical Property:

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Technology Process of p-methoxyphenyl O-[3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-levulinoyl-β-D-glucopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside

There total 12 articles about p-methoxyphenyl O-[3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-levulinoyl-β-D-glucopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-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: 73.0%

p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside (202864-95-7) + 4-Oxo-pentanoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (202864-97-9) → p-methoxyphenyl O-[3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-levulinoyl-β-D-glucopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside (202864-98-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -78 ℃; for 3.5h;

DOI:10.1016/S0040-4020(97)10377-5

Reference yield:

4,5-dichlorophthalic anhydride (942-06-3) → p-methoxyphenyl O-[3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-levulinoyl-β-D-glucopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside (202864-98-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) Et₃N, 2.) Ac₂O, pyridine / 1) 1,2-dichloroethane, 50-60 deg C, 2 h; 2) rt, 24 h

2: 87 percent / TMSOTf / 1,2-dichloro-ethane / 42 h

3: 25 g / NaOMe / methanol; CH₂Cl₂ / 4 h / 0 °C

4: 74 percent / camphorsulphonic acid / dimethylformamide / 60 h / Ambient temperature

5: 4 Angstroem molecular sieves, NaH / dimethylformamide / 28 h / 6 °C

6: 4 Angstroem molecular sieves, sodium cyanoborohydride, aq. HCl / tetrahydrofuran / 7 h / Ambient temperature

7: 95 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

8: 82 percent / ceriumammonium nitrate / toluene; acetonitrile; H₂O / 5 h / Ambient temperature

9: 4 Angstroem molecular sieves, 1,8-diazabicyclo<5.4.0>-undecen / CH₂Cl₂ / 1 h / Ambient temperature

10: 73 percent / 4 Angstroem molecular sieves, trimethylsilyl trifluoromethanesulphonate / CH₂Cl₂ / 3.5 h / -78 °C

With pyridine; hydrogenchloride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; acetic anhydride; sodium hydride; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(97)10377-5

Reference yield:

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) → p-methoxyphenyl O-[3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-levulinoyl-β-D-glucopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside (202864-98-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) Et₃N, 2.) Ac₂O, pyridine / 1) 1,2-dichloroethane, 50-60 deg C, 2 h; 2) rt, 24 h

2: 87 percent / TMSOTf / 1,2-dichloro-ethane / 42 h

3: 25 g / NaOMe / methanol; CH₂Cl₂ / 4 h / 0 °C

4: 74 percent / camphorsulphonic acid / dimethylformamide / 60 h / Ambient temperature

5: 4 Angstroem molecular sieves, NaH / dimethylformamide / 28 h / 6 °C

6: 4 Angstroem molecular sieves, sodium cyanoborohydride, aq. HCl / tetrahydrofuran / 7 h / Ambient temperature

7: 95 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

8: 82 percent / ceriumammonium nitrate / toluene; acetonitrile; H₂O / 5 h / Ambient temperature

9: 4 Angstroem molecular sieves, 1,8-diazabicyclo<5.4.0>-undecen / CH₂Cl₂ / 1 h / Ambient temperature

10: 73 percent / 4 Angstroem molecular sieves, trimethylsilyl trifluoromethanesulphonate / CH₂Cl₂ / 3.5 h / -78 °C

With pyridine; hydrogenchloride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; acetic anhydride; sodium hydride; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(97)10377-5

upstream raw materials:

p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside

4-Oxo-pentanoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

4,5-dichlorophthalic anhydride

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

Downstream raw materials:

p-methoxyphenyl O-[3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside

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