5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam

Base Information

• Chemical Name: 5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam
• CAS No.: 1363528-66-8
• Molecular Formula: C₄₉H₅₇NO₁₃
• Molecular Weight: 867.99

Synonyms:5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam

Chemical Property of 5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam

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Technology Process of 5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam

There total 6 articles about 5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam 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: 50.0%

phenyl 2-O-{3-[5-(4,6-O-benzylidene-β-D-glucopyranos-1-yloxy)pentylaminocarbonyl]propinonyl}-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside (1363528-54-4) → 5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam (1363528-66-8) + 5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-α-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam (1363528-69-1)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -10 - -5 ℃; Inert atmosphere;

DOI:10.3762/bjoc.7.189

Reference yield:

5-aminopentyl 4,6-O-benzylidene-β-D-glucopyranoside (1363528-42-0) → 5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam (1363528-66-8) + 5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-α-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam (1363528-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ethyl acetate / 16 h / 25 °C

2: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane; acetonitrile / -10 - -5 °C / Inert atmosphere

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.3762/bjoc.7.189

Reference yield:

phenyl 3,4,6-tri-O-benzyl-2-O-(3-pentafluorophenoxycarbonylpropionyl)-1-thio-β-D-galactopyranoside (1363528-28-2) → 5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam (1363528-66-8) + 5-aminopentyl 3,4,5-tri-O-benzyl-2-O-(3-carboxypropionyl)-α-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside ?-lactam (1363528-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ethyl acetate / 16 h / 25 °C

2: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane; acetonitrile / -10 - -5 °C / Inert atmosphere

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.3762/bjoc.7.189

upstream raw materials:

phenyl 2-O-{3-[5-(4,6-O-benzylidene-β-D-glucopyranos-1-yloxy)pentylaminocarbonyl]propinonyl}-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

phenyl 3,4,6-tri-O-benzyl-2-O-(3-pentafluorophenoxycarbonylpropionyl)-1-thio-β-D-galactopyranoside

5-aminopentyl 4,6-O-benzylidene-β-D-glucopyranoside

phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

5-(3-hydroxycarbonylpropanamido)pentyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-β-D-glucopyranoside

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