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

Base Information

• Chemical Name: 3-amino-3-N-benzyl-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-phenylmethanesulfonyl-α-D-ribofuranose
• CAS No.: 667923-36-6
• Molecular Formula: C₃₀H₃₀N₂O₇S
• Molecular Weight: 562.643
• Mol file: 667923-36-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 3-amino-3-N-benzyl-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-phenylmethanesulfonyl-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: 53.0%

benzyl bromide (100-39-0) + 3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-3-N-phenylmethanesulfonyl-1,2-O-isopropylidene-α-D-ribofuranose (667923-56-0) → 3-amino-3-N-benzyl-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-phenylmethanesulfonyl-α-D-ribofuranose (667923-36-6) + C30H30N2O7S

Guidance literature:

With potassium carbonate; In acetone; for 6h; Heating;

DOI:10.1021/jo035301g

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) → 3-amino-3-N-benzyl-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-phenylmethanesulfonyl-α-D-ribofuranose (667923-36-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Ti(OiPr)4; NH₄Cl; Et₃N / methanol

1.2: 82 percent / methanol

2.1: 97 percent / pyridine; DMAP / 0.5 h / 20 °C

3.1: 53 percent / K₂CO₃ / acetone / 6 h / Heating

With pyridine; titanium(IV) isopropylate; dmap; potassium carbonate; ammonium chloride; triethylamine; In methanol; acetone;

DOI:10.1021/jo035301g

Reference yield:

3-amino-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (302582-11-2) → 3-amino-3-N-benzyl-5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-phenylmethanesulfonyl-α-D-ribofuranose (667923-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine; DMAP / 0.5 h / 20 °C

2: 53 percent / K₂CO₃ / acetone / 6 h / Heating

With pyridine; dmap; potassium carbonate; In acetone;

DOI:10.1021/jo035301g

upstream raw materials:

benzyl bromide

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

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

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