Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 201287-88-9
• Molecular Formula: C₁₈H₁₉N₅O₆S
• Molecular Weight: 433.445

Synonyms:Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester

There total 4 articles about Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester 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: 55.0%

methanesulfonyl chloride (124-63-0) + Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (201287-87-8) → Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester (201287-88-9)

Guidance literature:

In pyridine; Ambient temperature;

DOI:10.1016/0960-894X(96)00293-4

Reference yield:

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester (201287-88-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / SnCl₄ / acetonitrile / Ambient temperature

2: 40 percent / CH₃ONa / tetrahydrofuran

3: 55 percent / pyridine

With pyridine; sodium methylate; tin(IV) chloride; In tetrahydrofuran; acetonitrile;

DOI:10.1080/07328319708006190

Reference yield:

Benzoic acid (2R,4S,5S)-4-acetoxy-5-(6-amino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester (201287-86-7) → Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester (201287-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / CH₃ONa / tetrahydrofuran

2: 55 percent / pyridine

With pyridine; sodium methylate; In tetrahydrofuran;

DOI:10.1080/07328319708006190

upstream raw materials:

methanesulfonyl chloride

Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

adenine

Benzoic acid (2R,4S,5S)-4-acetoxy-5-(6-amino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester

Downstream raw materials:

Benzoic acid (2R,5S)-5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-ylmethyl ester

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