5-O-benzyl-3-(4-bromobutanamido)-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

Base Information

• Chemical Name: 5-O-benzyl-3-(4-bromobutanamido)-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose
• CAS No.: 1355965-77-3
• Molecular Formula: C₂₀H₂₅BrN₂O₅
• Molecular Weight: 453.333

Synonyms:5-O-benzyl-3-(4-bromobutanamido)-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property of 5-O-benzyl-3-(4-bromobutanamido)-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property:

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Technology Process of 5-O-benzyl-3-(4-bromobutanamido)-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

There total 2 articles about 5-O-benzyl-3-(4-bromobutanamido)-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 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: 60.0%

4-bromobutyroyl chloride (927-58-2) + 3-amino-5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (302582-09-8) → 5-O-benzyl-3-(4-bromobutanamido)-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (1355965-77-3)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2011.11.067

Reference yield:

5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose (34311-63-2) → 5-O-benzyl-3-(4-bromobutanamido)-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (1355965-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: titanium(IV) isopropylate; ammonia / methanol

2: pyridine; dmap / 1 h / 20 °C / Inert atmosphere

With pyridine; titanium(IV) isopropylate; dmap; ammonia; In methanol;

DOI:10.1016/j.tet.2011.11.067

Reference yield: 90.0%

5-O-benzyl-3-(4-bromobutanamido)-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (1355965-77-3) → 5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-(2-oxopyrrolidine)-α-D-ribofuranose (1355965-86-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2011.11.067

upstream raw materials:

5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose

4-bromobutyroyl chloride

3-amino-5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

Downstream raw materials:

5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-(2-oxopyrrolidine)-α-D-ribofuranose

spiro[5-O-benzyl-3-deoxy-1,2-isopropylidene-α-D-ribofuranose-3,3'-(3',5',6',7'-tetrahydrospiro[cyclopropane-1,2'-pyrrolo[1,2-a]imidazole])]

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