1-(6-Chloro-9H-purin-9-yl)-1-deoxy-2,3-O-isopropylidene-beta-D-ribofuranuronoyl chloride

Base Information

• Chemical Name: 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-2,3-O-isopropylidene-beta-D-ribofuranuronoyl chloride
• CAS No.: 104940-65-0
• Molecular Formula: C₁₃H₁₂Cl₂N₄O₄
• Molecular Weight: 359.169
• Mol file: 104940-65-0.mol

Synonyms:(3aR,4R,6S,6aS)-4-(6-chloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carbonyl chloride;

Chemical Property of 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-2,3-O-isopropylidene-beta-D-ribofuranuronoyl chloride

Chemical Property:

• PSA: 88.36000
• Density: 1.87
• LogP: 1.66260
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

1-(6-Chloro-9H-purin-9-yl)-1-deoxy-2,3-O-(1-methylethylidene)-b-D-Ribofuranuronoylchloride 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-2,3-O-isopropylidene-beta-D-ribofuranuronoyl chloride

There total 4 articles about 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-2,3-O-isopropylidene-beta-D-ribofuranuronoyl chloride 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:

(3aS,4S,6R,6aR)-2,2-dimethyl-6-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (28440-13-3) → 1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride (104940-65-0)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In chloroform; for 6h; Heating;

DOI:10.1021/jm00159a020

Reference yield:

2',3'-O-isopropylideneinosine (2140-11-6) → 1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride (104940-65-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy free radical; iodosobenzene diacetate / acetonitrile; H₂O / 4 h / 20 °C

2: SOCl₂; DMF / CHCl₃ / 5 h / Heating

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

DOI:10.1021/jm061279i

Reference yield:

2',3'-isopropylideneinosine-5'-carboxylic acid → 1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride (104940-65-0)

Guidance literature:

With thionyl chloride; In chloroform; N,N-dimethyl-formamide; for 6h; Heating;

DOI:10.1021/jm00031a014

upstream raw materials:

(3aS,4S,6R,6aR)-2,2-dimethyl-6-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid

2',3'-O-isopropylideneinosine

Inosine

Downstream raw materials:

adenosine 5'-carboxamide

(2S,3S,4R,5R)-5-[6-((S)-1-Benzyl-propylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide

(2S,3S,4R,5R)-5-[6-((R)-1-Benzyl-propylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide

(2S,3S,4R,5R)-3,4-Dihydroxy-5-[6-((S)-1-methyl-2-phenyl-ethylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid ethylamide

Refernces

• 1、 Gallo-Rodriguez, Carola,Ji, Xiao-duo,Melman, Neli,Siegman, Barry D.,Sanders, Lawrence H.,et al.. "Structure-Activity Relationships of N6-Benzyladenosine-5'-uronamides as A3-Selective Adenosine Agonists". . p. 636 - 646. Retrieved 2007/10/02.