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

Base Information

• Chemical Name: ethyl 1-deoxy-1-[N⁶-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranuroate
• CAS No.: 849242-05-3
• Molecular Formula: C₂₃H₂₅ClIN₅O₅
• Molecular Weight: 613.839

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

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

Chemical Property:

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

There total 6 articles about ethyl 1-deoxy-1-[N⁶-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranuroate 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: 57.0%

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) + ethanol (64-17-5) → ethyl 1-deoxy-1-[N6-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranuroate (849242-05-3)

Guidance literature:

With thionyl chloride; at 20 ℃; for 7h;

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) → ethyl 1-deoxy-1-[N6-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranuroate (849242-05-3)

Guidance literature:

Multi-step reaction with 3 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

3: 57 percent / SOCl₂ / 7 h / 20 °C

With thionyl chloride; 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:

N6-(3-iodobenzyl)-2-chloro-9H-(2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranosyl)adenine (849242-02-0) → ethyl 1-deoxy-1-[N6-(3-iodobenzyl)-2-chloro-9H-purin-9-yl]-2-C-methyl-2,3-O-isopropylidene-β-D-ribofuranuroate (849242-05-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 57 percent / SOCl₂ / 7 h / 20 °C

With thionyl chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; water; In acetonitrile;

DOI:10.1021/jm049408n

upstream raw materials:

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

ethanol

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

Downstream raw materials:

(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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