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

Base Information

• Chemical Name: 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose
• CAS No.: 302582-11-2
• Molecular Formula: C₁₆H₁₈N₂O₅
• Molecular Weight: 318.329
• Mol file: 302582-11-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 3-amino-5-O-benzoyl-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: 82.0%

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) + trimethylsilyl cyanide (7677-24-9) → 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (302582-11-2)

Guidance literature:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose; With titanium(IV) isopropylate; ammonium chloride; triethylamine; In methanol;

trimethylsilyl cyanide; In methanol;

DOI:10.1021/jo035301g

Reference yield:

benzoic acid 2,2-dimethyl-6-oxo-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester → 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (302582-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₃; Ti(OiPr)4 / methanol / 20 °C

2: methanol / 12 h

With titanium(IV) isopropylate; ammonia; In methanol; 1: amination / 2: cyanation;

DOI:10.1016/S0040-4039(00)01090-X

Reference yield:

trimethylsilyl cyanide (7677-24-9) + Benzoic acid (3aR,5S,6aR)-6-imino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester → 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (302582-11-2)

Guidance literature:

In methanol; for 12h;

DOI:10.1016/S0040-4039(00)01090-X

upstream raw materials:

trimethylsilyl cyanide

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

Downstream raw materials:

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

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

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

1,2-O-isopropylidene-α-D-erythro-pentofuranose-3-spiro-3'-(4'-amino-5'-phenyl-5'H-2',3'-dihydroisothiazole-1',1'-dioxide)