2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
CAS No.:496052-71-2
Molecular Formula:C₆₄H₆₁Cl₃N₂O₁₂
Molecular Weight:1156.55
Hs Code.:

Synonyms:2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

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Technology Process of 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

There total 8 articles about 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-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: 92.0%

: 545-06-2
trichloroacetonitrile

: 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-D-glucopyranose

: 496052-71-2
2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -10 ℃; for 2h;
DOI:10.1271/bbb.66.1904

Reference yield:

: tert-butyldiphenylsilyl 2-phthalimido-3,6-di-O-benzyl-2-deoxy-β-D-dlucopyranoside

: 496052-71-2
2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h

1.2: 20 percent / AgOTf / CH₂Cl₂ / 1 h / -20 °C

2.1: 83 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 0.33 h / -10 °C

3.1: 0.86 g / NaOMe / methanol / 2 h / 20 °C

4.1: 84 percent / Bu₄NI; NaH / dimethylformamide / 4 h / 0 - 20 °C

5.1: 91 percent / AcOH; TBAF / tetrahydrofuran / 24 h / 20 °C

6.1: 92 percent / DBU / CH₂Cl₂ / 2 h / -10 °C

With 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1271/bbb.66.1904

Reference yield:

: 100-39-0
benzyl bromide

: 496052-71-2
2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / Bu₄NI; NaH / dimethylformamide / 4 h / 0 - 20 °C

2: 91 percent / AcOH; TBAF / tetrahydrofuran / 24 h / 20 °C

3: 92 percent / DBU / CH₂Cl₂ / 2 h / -10 °C

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1271/bbb.66.1904