3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-α-D-ribofuranose

Base Information

• Chemical Name: 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-α-D-ribofuranose
• CAS No.: 332366-77-5
• Molecular Formula: C₁₇H₂₀N₂O₇S
• Molecular Weight: 396.421

Synonyms:3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-α-D-ribofuranose

Chemical Property of 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-α-D-ribofuranose

Chemical Property:

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Technology Process of 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-α-D-ribofuranose

There total 2 articles about 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-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: 98.0%

methanesulfonyl chloride (124-63-0) + 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (302582-11-2) → 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-α-D-ribofuranose (332366-77-5)

Guidance literature:

With pyridine; dmap;

DOI:10.1016/S0040-4039(00)02013-X

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) → 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-α-D-ribofuranose (332366-77-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / Ti(OiPr)4; NH₃ / methanol

2: 95 percent / pyridine; DMAP

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

DOI:10.1021/jm050091g

Reference yield: 99.0%

3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-α-D-ribofuranose (332366-77-5) → 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-N-mesyl-D-ribofuranose

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 2h;

DOI:10.1021/jm050091g

upstream raw materials:

methanesulfonyl chloride

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

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose

Downstream raw materials:

3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-3-N-methyl-α-D-ribofuranose

(1S,3R,7R,8R,12S,14R)-12-amino-9-N-benzyl-5,5-dimethyl-10-thia-10,10-dioxide-9-aza-2,4,6,13-tetraoxatetracyclo[6.6.0.0^3,7.0^8,12]tetradecane

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