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-α-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name: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-α-D-glucopyranosyl trichloroacetimidate
CAS No.:1448540-31-5
Molecular Formula:C₅₀H₄₄Cl₄N₂O₁₇
Molecular Weight:1086.71
Hs Code.:

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-α-D-glucopyranosyl trichloroacetimidate

Synonyms: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-α-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 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-α-D-glucopyranosyl trichloroacetimidate

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Technology Process of 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-α-D-glucopyranosyl trichloroacetimidate

There total 19 articles about 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-α-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:

: C₄₈H₄₄ClNO₁₇

: 545-06-2
trichloroacetonitrile

: 1448540-31-5
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-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1021/jo4012442

Reference yield:

: 14131-63-6
D-glucosamine hydrochloride

: 1448540-31-5
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-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 11 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: ammonium cerium (IV) nitrate / water; acetonitrile / 0.67 h / 0 °C

11: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 3 h / 0 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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

: 1448540-31-5
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-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 9 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: ammonium cerium (IV) nitrate / water; acetonitrile / 0.67 h / 0 °C

9: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 3 h / 0 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo4012442