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

Base Information

• Chemical Name: 3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose
• CAS No.: 332366-75-3
• Molecular Formula: C₂₉H₃₀N₂O₆S
• Molecular Weight: 534.633
• Mol file: 332366-75-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about 3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-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: 92.0%

methanesulfonyl chloride (124-63-0) + 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose (302582-03-2) → 3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (332366-75-3)

Guidance literature:

With pyridine; dmap;

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

Reference yield:

1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose (20590-54-9) → 3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (332366-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NH₃; Ti(OiPr)4 / methanol / 5 h / 20 °C

1.2: 96 percent / methanol / 12 h

2.1: 92 percent / DMAP; pyridine / 5 h / 20 °C

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

DOI:10.1016/j.tet.2004.03.063

Reference yield: 99.0%

3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (332366-75-3) + methyl iodide (74-88-4) → 3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-3-N-methyl-5-O-trityl-α-D-ribofuranose (332366-79-7)

Guidance literature:

With potassium carbonate; In acetone; for 2h; Heating;

DOI:10.1016/j.tet.2004.03.063

upstream raw materials:

methanesulfonyl chloride

3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose

1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose

Downstream raw materials:

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

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

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

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