p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 220449-96-7
• Molecular Formula: C₇₀H₇₅NO₂₁
• Molecular Weight: 1266.36

Synonyms:p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

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Technology Process of p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 5 articles about p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-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: 76.0%

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) + p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (220449-95-6) → p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (220449-96-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; In dichloromethane; at -70 - -30 ℃; for 3h;

DOI:10.1080/07328300008544072

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (220449-96-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / TsOH / acetonitrile / 0.5 h / 20 °C

2: 97 percent / tetrabutylammonium bromide; diisopropylamine / CH₂Cl₂; dimethylformamide / 4 h / 20 °C

3: 74 percent / sodium cyanoborohydride; molecular sieves 3 Angstroem; HCl / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C / pH 1

4: 76 percent / molecular sieves 3 Angstroem; trimethylsilyl triflate / CH₂Cl₂ / 3 h / -70 - -30 °C

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; tetrabutylammomium bromide; sodium cyanoborohydride; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: acetal formation / 2: Substitution / 3: Reduction / 4: glycosylation;

DOI:10.1080/07328300008544072

Reference yield:

p-methoxybenzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (93417-35-7) → p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (220449-96-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / TsOH / acetonitrile / 0.5 h / 20 °C

2: 97 percent / tetrabutylammonium bromide; diisopropylamine / CH₂Cl₂; dimethylformamide / 4 h / 20 °C

3: 74 percent / sodium cyanoborohydride; molecular sieves 3 Angstroem; HCl / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C / pH 1

4: 76 percent / molecular sieves 3 Angstroem; trimethylsilyl triflate / CH₂Cl₂ / 3 h / -70 - -30 °C

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; tetrabutylammomium bromide; sodium cyanoborohydride; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: acetal formation / 2: Substitution / 3: Reduction / 4: glycosylation;

DOI:10.1080/07328300008544072

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

benzaldehyde dimethyl acetal

p-methoxybenzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

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

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

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