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

Base Information

Chemical Name:methyl O-(2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-3-O-methyl-4,6-di-O-benzyl-α-D-mannopyranoside
CAS No.:161767-11-9
Molecular Formula:C₄₂H₄₇NO₁₅
Molecular Weight:805.833
Hs Code.:

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

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

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

There total 3 articles about methyl O-(2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-3-O-methyl-4,6-di-O-benzyl-α-D-mannopyranoside 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: 80.0%

: 10028-45-2
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide

: 161767-10-8
methyl 3-O-methyl-4,6-di-O-benzyl-α-D-mannopyranoside

: 161767-11-9
methyl O-(2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-3-O-methyl-4,6-di-O-benzyl-α-D-mannopyranoside

Guidance literature:: With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -50 - 20 ℃; for 2.25h;
DOI:10.1016/S0957-4166(00)80389-4

Reference yield:

: 84553-74-2
methyl 4,6-di-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside

: 161767-11-9
methyl O-(2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-3-O-methyl-4,6-di-O-benzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / aq. CF₃CO₂H / CHCl₃ / 4 h / Ambient temperature

2: 1.) dibutyltin oxide, 2.) Bu₄NI / 1.) MeOH, reflux, 2 h, 2.) toluene, 60 deg C, 16 h

3: 80 percent / silver trifluoromethanesulfonate, sym-collidine, mol. sieves 4A / CH₂Cl₂ / 2.25 h / -50 - 20 °C

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; trifluoroacetic acid; In dichloromethane; chloroform;
DOI:10.1016/S0957-4166(00)80389-4

Reference yield:

: 63167-69-1
methyl 2,3-O-isopropylidene-α-D-mannopyranoside

: 161767-11-9
methyl O-(2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-3-O-methyl-4,6-di-O-benzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, RT, 0.5 h, 2.) DMF, RT, 24 h

2: 86 percent / aq. CF₃CO₂H / CHCl₃ / 4 h / Ambient temperature

3: 1.) dibutyltin oxide, 2.) Bu₄NI / 1.) MeOH, reflux, 2 h, 2.) toluene, 60 deg C, 16 h

4: 80 percent / silver trifluoromethanesulfonate, sym-collidine, mol. sieves 4A / CH₂Cl₂ / 2.25 h / -50 - 20 °C

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; trifluoroacetic acid; In dichloromethane; chloroform;
DOI:10.1016/S0957-4166(00)80389-4