3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-methyl-3-N-phenylmethanesulfonyl-α-D-allofuranose

Base Information

• Chemical Name: 3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-methyl-3-N-phenylmethanesulfonyl-α-D-allofuranose
• CAS No.: 721924-39-6
• Molecular Formula: C₂₁H₂₈N₂O₇S
• Molecular Weight: 452.529

Synonyms:3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-methyl-3-N-phenylmethanesulfonyl-α-D-allofuranose

Chemical Property of 3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-methyl-3-N-phenylmethanesulfonyl-α-D-allofuranose

Chemical Property:

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Technology Process of 3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-methyl-3-N-phenylmethanesulfonyl-α-D-allofuranose

There total 2 articles about 3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-methyl-3-N-phenylmethanesulfonyl-α-D-allofuranose 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: 95.0%

methyl iodide (74-88-4) + 3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-phenylmethanesulfonyl-α-D-allofuranose (721924-36-3) → 3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-methyl-3-N-phenylmethanesulfonyl-α-D-allofuranose (721924-39-6)

Guidance literature:

With potassium carbonate; In acetone; for 4h; Heating;

DOI:10.1016/j.tet.2004.03.063

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → 3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-methyl-3-N-phenylmethanesulfonyl-α-D-allofuranose (721924-39-6)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 98 percent / methanol / 12 h

2.1: 60 percent / DMAP; pyridine / 30 h / 20 °C

3.1: 95 percent / potassium carbonate / acetone / 4 h / Heating

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

DOI:10.1016/j.tet.2004.03.063

Reference yield: 96.0%

3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-methyl-3-N-phenylmethanesulfonyl-α-D-allofuranose (721924-39-6) → 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose-3-spiro-3'-(4'-amino-2'-N-methyl-5'-phenyl-5'H-2',3'-dihydroisothiazole-1',1'-dioxide) (721924-50-1)

Guidance literature:

With caesium carbonate; In acetonitrile; for 2h; Heating;

DOI:10.1016/j.tet.2004.03.063

upstream raw materials:

methyl iodide

3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-N-phenylmethanesulfonyl-α-D-allofuranose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

Downstream raw materials:

1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose-3-spiro-3'-(4'-amino-2'-N-methyl-5'-phenyl-5'H-2',3'-dihydroisothiazole-1',1'-dioxide)

1,2-O-isopropylidene-α-D-ribo-hexofuranose-3-spiro-3'-(4'-amino-2'-N-methyl-5'-phenyl-5'H-2',3'-dihydroisothiazole-1',1'-dioxide)

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