O-(4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-phthalimido-α,β-D-glucopyranosyl) trichloroacetimidate

Base Information

• Chemical Name: O-(4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-phthalimido-α,β-D-glucopyranosyl) trichloroacetimidate
• CAS No.: 1225291-44-0
• Molecular Formula: C₂₈H₂₅Cl₃N₂O₉
• Molecular Weight: 639.873

Synonyms:O-(4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-phthalimido-α,β-D-glucopyranosyl) trichloroacetimidate

Chemical Property of O-(4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-phthalimido-α,β-D-glucopyranosyl) trichloroacetimidate

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Technology Process of O-(4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-phthalimido-α,β-D-glucopyranosyl) trichloroacetimidate

There total 2 articles about O-(4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-phthalimido-α,β-D-glucopyranosyl) trichloroacetimidate 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: 76.0%

4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-phthalimido-α,β-D-glucopyranose + trichloroacetonitrile (545-06-2) → O-(4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-phthalimido-α,β-D-glucopyranosyl) trichloroacetimidate (1225291-44-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2018.01.022

Reference yield:

C33H31NO10 → O-(4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-phthalimido-α,β-D-glucopyranosyl) trichloroacetimidate (1225291-44-0)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium cerium (IV) nitrate / dichloromethane; water; acetonitrile / 1.5 h / 0 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C

With ammonium cerium (IV) nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.bmc.2018.01.022

Reference yield: 92.0%

O-(4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-phthalimido-α,β-D-glucopyranosyl) trichloroacetimidate (1225291-44-0) + 4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-6-O-4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoyl-β-D-glucopyranoside → C64H54F17NO17

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1.5h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.bmc.2018.01.022

upstream raw materials:

trichloroacetonitrile

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