(3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid

Base Information

• Chemical Name: (3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid
• CAS No.: 120355-42-2
• Molecular Formula: C₁₃H₁₃ClN₄O₅
• Molecular Weight: 340.723
• Mol file: 120355-42-2.mol

Synonyms:(3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid

Chemical Property of (3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid

There total 2 articles about (3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic 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: 100.0%

6-chloro-9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine (39824-26-5) → (3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (120355-42-2)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; Ambient temperature;

DOI:10.1016/S0040-4039(00)74197-9

Reference yield:

6-Chloropurine riboside (2004-06-0) → (3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (120355-42-2)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / acetone / 2 h / 20 °C

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / 4 h / 40 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid; In water; acetone; acetonitrile;

DOI:10.1002/cmdc.201100126

Reference yield: 98.5%

(3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (120355-42-2) + 3-amino-4-hydroxytoluene (95-84-1) → 6-[6-(2-hydroxy-5-methylphenylamino)purin-9-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid

Guidance literature:

With N-ethyl-N,N-diisopropylamine; at 80 ℃; for 12h;

DOI:10.3390/molecules23051111

upstream raw materials:

6-chloro-9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine

6-Chloropurine riboside

Downstream raw materials:

2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide

C₂₂H₂₆N₆O₅

3,4-dihydroxy-5-[6-(4-hydroxybenzylamino)purin-9-yl]tetrahydrofuran-2-carboxylic acid ethylamide

C₂₁H₂₂N₆O₄

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