methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->6)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)]-3,4-di-O-benzyl-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->6)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)]-3,4-di-O-benzyl-β-D-galactopyranoside
• CAS No.: 273397-31-2
• Molecular Formula: C₆₈H₇₃NO₁₉
• Molecular Weight: 1208.32

Synonyms:methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->6)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)]-3,4-di-O-benzyl-β-D-galactopyranoside

Chemical Property of methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->6)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)]-3,4-di-O-benzyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->6)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)]-3,4-di-O-benzyl-β-D-galactopyranoside

There total 4 articles about methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->6)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)]-3,4-di-O-benzyl-β-D-galactopyranoside 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: 61.0%

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (174314-07-9) + methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4-di-O-benzyl-β-D-galactopyranoside (273397-28-7) → methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->6)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)]-3,4-di-O-benzyl-β-D-galactopyranoside (273397-31-2)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1080/07328300008544077

Reference yield:

methyl 3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside (2774-19-8,14419-69-3,15887-67-9,23392-28-1,57539-08-9,61277-63-2,65877-21-6,74410-51-8,76419-48-2,80734-73-2,86363-44-2,89301-79-1,94061-92-4,108739-92-0,129706-93-0,143005-12-3,94062-87-0) → methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->6)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)]-3,4-di-O-benzyl-β-D-galactopyranoside (273397-31-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / CuBr₂; Bu₄NBr; molecular sieves 4 Angstroem / CH₂Cl₂; dimethylformamide / 48 h / 20 °C

2: 70 percent / LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 0.75 h / Heating

3: 61 percent / N-iodosuccinimide; molecular sieves 4 Angstroem; TfOH / CH₂Cl₂ / 4 h / 0 °C

With N-iodo-succinimide; lithium aluminium tetrahydride; aluminium trichloride; trifluorormethanesulfonic acid; 4 A molecular sieve; tetrabutylammomium bromide; copper(ll) bromide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Reduction / 3: Substitution;

DOI:10.1080/07328300008544077

Reference yield:

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8) → methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->6)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)]-3,4-di-O-benzyl-β-D-galactopyranoside (273397-31-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / CuBr₂; Bu₄NBr; molecular sieves 4 Angstroem / CH₂Cl₂; dimethylformamide / 48 h / 20 °C

2: 70 percent / LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 0.75 h / Heating

3: 61 percent / N-iodosuccinimide; molecular sieves 4 Angstroem; TfOH / CH₂Cl₂ / 4 h / 0 °C

With N-iodo-succinimide; lithium aluminium tetrahydride; aluminium trichloride; trifluorormethanesulfonic acid; 4 A molecular sieve; tetrabutylammomium bromide; copper(ll) bromide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Reduction / 3: Substitution;

DOI:10.1080/07328300008544077

upstream raw materials:

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4-di-O-benzyl-β-D-galactopyranoside

methyl 3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

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