3-amino-3-N-benzyl-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-N-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose
• CAS No.: 721924-31-8
• Molecular Formula: C₃₆H₃₆N₂O₆S
• Molecular Weight: 624.758

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

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

Chemical Property:

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Technology Process of 3-amino-3-N-benzyl-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-N-benzyl-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: 66.0%

benzyl bromide (100-39-0) + 3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (332366-75-3) → 3-amino-3-N-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (721924-31-8)

Guidance literature:

With potassium carbonate; In acetone; for 19h; Heating;

DOI:10.1016/j.tet.2004.03.063

Reference yield:

1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose (20590-54-9) → 3-amino-3-N-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (721924-31-8)

Guidance literature:

Multi-step reaction with 3 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

3.1: 66 percent / potassium carbonate / acetone / 19 h / Heating

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

DOI:10.1016/j.tet.2004.03.063

Reference yield: 46.0%

3-amino-3-N-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose (721924-31-8) → 1,2-O-isopropylidene-5-O-trityl-α-D-erythro-pentofuranose-3-spiro-3'-(4'-amino-2'-N-benzyl-5'H-2',3'-dihydroisothiazole-1',1'-dioxide) (721924-42-1)

Guidance literature:

With caesium carbonate; In acetonitrile; for 3h; Heating;

DOI:10.1016/j.tet.2004.03.063

upstream raw materials:

benzyl bromide

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-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose

Downstream raw materials:

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

(1S,3R,7R,8R,12S,14R)-12-amino-9-N-benzyl-5,5-dimethyl-10-thia-10,10-dioxide-9-aza-2,4,6,13-tetraoxatetracyclo[6.6.0.0^3,7.0^8,12]tetradecane

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