3-N-allyl-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-N-allyl-3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose
• CAS No.: 721924-32-9
• Molecular Formula: C₃₂H₃₄N₂O₆S
• Molecular Weight: 574.698

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

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

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Technology Process of 3-N-allyl-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-N-allyl-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: 56.0%

allyl bromide (106-95-6) + 3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (332366-75-3) → 3-N-allyl-3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (721924-32-9)

Guidance literature:

With potassium carbonate; In acetone; for 24h; Heating;

DOI:10.1016/j.tet.2004.03.063

Reference yield:

3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose (302582-03-2) → 3-N-allyl-3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (721924-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / DMAP; pyridine / 5 h / 20 °C

2: 56 percent / potassium carbonate / acetone / 24 h / Heating

With pyridine; dmap; potassium carbonate; In acetone;

DOI:10.1016/j.tet.2004.03.063

Reference yield: 95.0%

3-N-allyl-3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (721924-32-9) → 1,2-O-isopropylidene-5-O-trityl-α-D-erythro-pentofuranose-3-spiro-3'-(2'-N-allyl-4'-amino-5'H-2',3'-dihydroisothiazole-1',1'-dioxide)

Guidance literature:

With caesium carbonate; In acetonitrile; for 1.33333h; Heating;

DOI:10.1016/j.tet.2004.03.063

upstream raw materials:

allyl bromide

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

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

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