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

Base Information

• Chemical Name: phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 424820-77-9
• Molecular Formula: C₅₄H₅₃NO₁₀S
• Molecular Weight: 908.082

Synonyms:phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Technology Process of phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 2 articles about phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-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:

phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (127061-09-0) → phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (424820-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 83.4 percent / N-iodosuccinimide; TfOH / CH₂Cl₂ / 0.5 h / -20 °C

2: 80.6 percent / H₃B*NMe₃; AlCl₃ / tetrahydrofuran / 8 h / 0 - 20 °C

With N-iodo-succinimide; aluminium trichloride; trifluorormethanesulfonic acid; trimethylamine-borane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0167396

Reference yield:

phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside (183875-25-4) → phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (424820-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 83.4 percent / N-iodosuccinimide; TfOH / CH₂Cl₂ / 0.5 h / -20 °C

2: 80.6 percent / H₃B*NMe₃; AlCl₃ / tetrahydrofuran / 8 h / 0 - 20 °C

With N-iodo-succinimide; aluminium trichloride; trifluorormethanesulfonic acid; trimethylamine-borane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0167396

Reference yield: 89.0%

[1-13C]-acetic acid (1563-79-7) + phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (424820-77-9) → phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-4-O-(acetyl-1-13C)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (220691-39-4)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/ja0167396

upstream raw materials:

phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside

Downstream raw materials:

phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-4-O-(acetyl-1-13C)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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