1-deoxy-1-[N⁶-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranoic acid

Base Information

• Chemical Name: 1-deoxy-1-[N⁶-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranoic acid
• CAS No.: 849242-03-1
• Molecular Formula: C₂₁H₂₁ClIN₅O₅
• Molecular Weight: 585.786

Synonyms:1-deoxy-1-[N⁶-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranoic acid

Chemical Property of 1-deoxy-1-[N⁶-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranoic acid

Chemical Property:

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Technology Process of 1-deoxy-1-[N⁶-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranoic acid

There total 5 articles about 1-deoxy-1-[N⁶-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranoic acid 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: 90.0%

N6-(3-iodobenzyl)-2-chloro-9H-(2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranosyl)adenine (849242-02-0) → 1-deoxy-1-[N6-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranoic acid (849242-03-1)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; water; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1021/jm049408n

Reference yield:

(2R,3R,4R,5R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol (849241-80-1) → 1-deoxy-1-[N6-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranoic acid (849242-03-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / camphorsulfonic acid / acetone / 6 h / 55 °C

2: 90 percent / diacetoxyiodobenzene; 2,2,6,6-tetramethylpiperidin-1-yloxy; water / acetonitrile / 3 h / 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; water; In acetone; acetonitrile;

DOI:10.1021/jm049408n

Reference yield:

C39H31ClIN5O7 → 1-deoxy-1-[N6-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranoic acid (849242-03-1)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₃ / methanol / 20 °C

2: 89 percent / camphorsulfonic acid / acetone / 6 h / 55 °C

3: 90 percent / diacetoxyiodobenzene; 2,2,6,6-tetramethylpiperidin-1-yloxy; water / acetonitrile / 3 h / 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; ammonia; water; In methanol; acetone; acetonitrile;

DOI:10.1021/jm049408n

upstream raw materials:

N⁶-(3-iodobenzyl)-2-chloro-9H-(2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranosyl)adenine

(2R,3R,4R,5R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

3-iodobenzylamine hydrochloride

2,6-dichloro-9-(2-C-methyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine

Downstream raw materials:

ethyl 1-deoxy-1-[N⁶-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranuroate

(2S,3R,4R,5R)-5-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-dihydroxy-4-methyl-tetrahydro-furan-2-carboxylic acid methylamide

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