p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside

Base Information

Chemical Name:p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside
CAS No.:1448540-30-4
Molecular Formula:C₅₃H₄₉NO₁₇
Molecular Weight:971.969
Hs Code.:

Synonyms:p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside

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Chemical Property of p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside

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Technology Process of p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside

There total 19 articles about p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-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%

: 1448540-29-1
p-methoxyphenyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside

: 1448540-30-4
p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: With 2,4-lutidine; thiourea; In methanol; dichloromethane; for 6h; Reflux;
DOI:10.1021/jo4012442

Reference yield:

: 14131-63-6
D-glucosamine hydrochloride

: 1448540-30-4
p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: sodium hydroxide / water

2: pyridine

3: boron trifluoride diethyl etherate / dichloromethane / 1 h / Reflux

4: sodium methylate / methanol / 3 h / 20 °C

5: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 1.5 h / 70 °C

6: pyridine / dichloromethane / 0.67 h / 0 °C

7: ammonium cerium (IV) nitrate / water; acetonitrile / 0.67 h / 0 °C

8: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 °C

9: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -30 - 0 °C / Molecular sieve; Inert atmosphere

10: thiourea; 2,4-lutidine / dichloromethane; methanol / 6 h / Reflux

With pyridine; ammonium cerium (IV) nitrate; 2,4-lutidine; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; thiourea; sodium hydroxide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo4012442

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 1448540-30-4
p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: boron trifluoride diethyl etherate / dichloromethane / 1 h / Reflux

2: sodium methylate / methanol / 3 h / 20 °C

3: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 1.5 h / 70 °C

4: pyridine / dichloromethane / 0.67 h / 0 °C

5: ammonium cerium (IV) nitrate / water; acetonitrile / 0.67 h / 0 °C

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 °C

7: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -30 - 0 °C / Molecular sieve; Inert atmosphere

8: thiourea; 2,4-lutidine / dichloromethane; methanol / 6 h / Reflux

With pyridine; ammonium cerium (IV) nitrate; 2,4-lutidine; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; thiourea; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo4012442