2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-methoxycarbonyl)propylcarbonylamino]-D-glycero-D-ido-heptitol

Base Information

• Chemical Name: 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-methoxycarbonyl)propylcarbonylamino]-D-glycero-D-ido-heptitol
• CAS No.: 701981-12-6
• Molecular Formula: C₄₁H₄₇NO₈
• Molecular Weight: 681.826

Synonyms:2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-methoxycarbonyl)propylcarbonylamino]-D-glycero-D-ido-heptitol

Chemical Property of 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-methoxycarbonyl)propylcarbonylamino]-D-glycero-D-ido-heptitol

Chemical Property:

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Technology Process of 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-methoxycarbonyl)propylcarbonylamino]-D-glycero-D-ido-heptitol

There total 2 articles about 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-methoxycarbonyl)propylcarbonylamino]-D-glycero-D-ido-heptitol 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:

Pentanedioic acid, monomethyl ester (1501-27-5) + 1-amino-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol (103977-05-5) → 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-methoxycarbonyl)propylcarbonylamino]-D-glycero-D-ido-heptitol (701981-12-6)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In dichloromethane; at 0 ℃; for 8h;

DOI:10.1081/CAR-120030022

Reference yield:

2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-ido-heptononitrile (71119-79-4) → 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-methoxycarbonyl)propylcarbonylamino]-D-glycero-D-ido-heptitol (701981-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94.4 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / 20 °C

2: 0.27 g / triethylamine; diphenylphosphoryl azide / CH₂Cl₂ / 8 h / 0 °C

With lithium aluminium tetrahydride; diphenylphosphoranyl azide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1081/CAR-120030022

Reference yield: 72.5%

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-methoxycarbonyl)propylcarbonylamino]-D-glycero-D-ido-heptitol (701981-12-6) → 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-oxopentyl-5-hydroxy)amino]-D-glycero-D-ido-heptitol (701981-13-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1081/CAR-120030022

upstream raw materials:

Pentanedioic acid, monomethyl ester

1-amino-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol

2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-ido-heptononitrile

Downstream raw materials:

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-oxopentyl-5-hydroxy)amino]-D-glycero-D-ido-heptitol

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