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

Base Information

• Chemical Name: N-phenyloxycarbonyl-3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-ribofuranose
• CAS No.: 330196-72-0
• Molecular Formula: C₃₅H₃₂N₂O₆
• Molecular Weight: 576.649
• Mol file: 330196-72-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about N-phenyloxycarbonyl-3-amino-3-C-cyano-3-deoxy-5-O-trityl-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: 83.0%

phenyl chloroformate (1885-14-9) + 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose (302582-03-2) → N-phenyloxycarbonyl-3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-ribofuranose (330196-72-0)

Guidance literature:

With potassium carbonate; In water; acetone;

DOI:10.1016/S0040-4039(00)02294-2 DOI:10.1211/0022357011776342

Reference yield:

1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose (20590-54-9) → N-phenyloxycarbonyl-3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-ribofuranose (330196-72-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NH₃; Ti(OiPr)4 / methanol / 2 h / 20 °C

1.2: 98 percent / methanol / 2 h

2.1: 83 percent / K₂CO₃ / acetone; H₂O

With titanium(IV) isopropylate; ammonia; potassium carbonate; In methanol; water; acetone;

DOI:10.1211/0022357011776342

Reference yield: 85.0%

N-phenyloxycarbonyl-3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-ribofuranose (330196-72-0) → (3R)-3,3-(1,3-diazaspiro-2,4-dioxo)-5-O-trityl-1,2-O-isopropylidene-α-D-ribofuranose (330196-73-1)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 80 ℃;

DOI:10.1016/S0040-4039(00)02294-2

upstream raw materials:

phenyl chloroformate

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:

(3R)-3,3-(1,3-diazaspiro-2,4-dioxo)-5-O-trityl-1,2-O-isopropylidene-α-D-ribofuranose