methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS No.: 181023-19-8
• Molecular Formula: C₃₆H₃₉NO₁₇
• Molecular Weight: 757.702
• Mol file: 181023-19-8.mol

Synonyms:methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Chemical Property of methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

There total 4 articles about methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 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: 95.0%

methanol (67-56-1) + phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside (181023-18-7) → methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (181023-19-8)

Guidance literature:

With 4 A molecular sieve; tris(p-bromophenylammoniumyl) hexachloroantimonate; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1016/S0957-4166(98)00246-8

Reference yield:

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (136882-36-5,79528-50-0) → methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (181023-19-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) (Bu₃Sn)2O / 1.) toluene, reflux, 15 h, 2.) toluene, RT, 5 h

2: 70 percent / AgOTf, SnCl₂, molecular sieves 4 Angstroem / toluene; CH₂Cl₂ / 2 h / -15 - 20 °C

3: 95 percent / tris (4-bromophenyl) ammoniumyl hexachloroantimonate, molecular sieves 4 Angstroem / acetonitrile / 1 h / Ambient temperature

With 4 A molecular sieve; silver trifluoromethanesulfonate; tris(p-bromophenylammoniumyl) hexachloroantimonate; bis(tri-n-butyltin)oxide; tin(ll) chloride; In dichloromethane; toluene; acetonitrile;

DOI:10.1016/S0957-4166(98)00246-8

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-49-7) → methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (181023-19-8)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOMe, MeOH / 2 h / Ambient temperature

2: 1.) (Bu₃Sn)2O / 1.) toluene, reflux, 15 h, 2.) toluene, RT, 5 h

3: 70 percent / AgOTf, SnCl₂, molecular sieves 4 Angstroem / toluene; CH₂Cl₂ / 2 h / -15 - 20 °C

4: 95 percent / tris (4-bromophenyl) ammoniumyl hexachloroantimonate, molecular sieves 4 Angstroem / acetonitrile / 1 h / Ambient temperature

With methanol; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; tris(p-bromophenylammoniumyl) hexachloroantimonate; bis(tri-n-butyltin)oxide; tin(ll) chloride; In dichloromethane; toluene; acetonitrile;

DOI:10.1016/S0957-4166(98)00246-8

upstream raw materials:

methanol

phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside

N-[(2R,3R,4R,5S,6R)-6-Hydroxymethyl-2-methoxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide