O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl trichloroacetimidate

Base Information

Chemical Name:O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl trichloroacetimidate
CAS No.:165061-09-6
Molecular Formula:C₃₉H₄₁Cl₃N₂O₁₇
Molecular Weight:916.117
Hs Code.:

Synonyms:O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl trichloroacetimidate

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Chemical Property of O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl trichloroacetimidate

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Technology Process of O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl trichloroacetimidate

There total 9 articles about O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl 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: 82.0%

: 545-06-2
trichloroacetonitrile

: 165061-08-5
O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-2,4-di-O-acetyl-3-O-benzyl-α-D-mannopyranoside

: 165061-09-6
O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 4h; Ambient temperature;
DOI:10.1016/0008-6215(94)00369-Q

Reference yield:

: 99409-32-2
ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 165061-09-6
O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1: 61 percent / 4A molecular sieves, MeOTf / CH₂Cl₂ / 15 h / Ambient temperature

2: 80 percent / AcOH / 0.5 h / 90 °C

3: 90 percent / pyridine / 2 h / Ambient temperature

4: 10percent Pd/C / methanol / 7 h / 70 °C

5: HgCl₂, HgO / acetone; H₂O / 0.33 h / Ambient temperature

6: 82 percent / DBU / CH₂Cl₂ / 4 h / Ambient temperature

With pyridine; palladium on activated charcoal; 4 A molecular sieve; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; methyl trifluoromethanesulfonate; mercury dichloride; mercury(II) oxide; In methanol; dichloromethane; water; acetone;
DOI:10.1016/0008-6215(94)00369-Q

Reference yield:

: 100-39-0
benzyl bromide

: 165061-09-6
O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) n-Bu₂SnO, 2.) n-Bu₄NI, 3.) aq. KF

2: 61 percent / 4A molecular sieves, MeOTf / CH₂Cl₂ / 15 h / Ambient temperature

3: 80 percent / AcOH / 0.5 h / 90 °C

4: 90 percent / pyridine / 2 h / Ambient temperature

5: 10percent Pd/C / methanol / 7 h / 70 °C

6: HgCl₂, HgO / acetone; H₂O / 0.33 h / Ambient temperature

7: 82 percent / DBU / CH₂Cl₂ / 4 h / Ambient temperature

With pyridine; potassium fluoride; palladium on activated charcoal; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; methyl trifluoromethanesulfonate; mercury dichloride; mercury(II) oxide; In methanol; dichloromethane; water; acetone;
DOI:10.1016/0008-6215(94)00369-Q