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

Base Information

• Chemical Name: 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose
• CAS No.: 302582-03-2
• Molecular Formula: C₂₈H₂₈N₂O₄
• Molecular Weight: 456.541
• Mol file: 302582-03-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose 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%

1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose (20590-54-9) + trimethylsilyl cyanide (7677-24-9) → 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose (302582-03-2)

Guidance literature:

1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose; With titanium(IV) isopropylate; ammonia; In methanol; at 20 ℃; for 2h;

trimethylsilyl cyanide; In methanol; for 2h;

DOI:10.1211/0022357011776342

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-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose (302582-03-2)

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) + (3aR,5S,6aR)-2,2-Dimethyl-5-trityloxymethyl-dihydro-furo[2,3-d][1,3]dioxol-6-ylideneamine → 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose (302582-03-2)

Guidance literature:

In methanol; for 12h;

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

upstream raw materials:

trimethylsilyl cyanide

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

Downstream raw materials:

1,2-O-isopropylidene-3-amino-3-deoxy-5-O-trityl-α-D-ribofuranoside

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

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

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