2-CHLORO-9-(2-3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYLURONIC ACID)ADENINE

Base Information

• Chemical Name: 2-CHLORO-9-(2-3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYLURONIC ACID)ADENINE
• CAS No.: 72209-19-9
• Molecular Formula: C₁₃H₁₄ClN₅O₅
• Molecular Weight: 355.738
• Mol file: 72209-19-9.mol

Synonyms:Furo[3,4-d]-1,3-dioxole,b-D-ribofuranuronic acid deriv.

Chemical Property of 2-CHLORO-9-(2-3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYLURONIC ACID)ADENINE

Chemical Property:

• Melting Point: 250-253 °C
• Boiling Point: 610.0±65.0 °C(Predicted)
• PKA: 2?+-.0.60(Predicted)
• PSA: 134.61000
• Density: 2.01±0.1 g/cm3(Predicted)
• LogP: 1.14520
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

97% ^*data from raw suppliers

(3AS,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-CHLORO-9-(2-3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYLURONIC ACID)ADENINE

There total 5 articles about 2-CHLORO-9-(2-3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYLURONIC ACID)ADENINE 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: 74.0%

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (24639-06-3) → 2-chloro-2',3'-O-isopropylideneadenosine-5'-carboxylic acid (72209-19-9)

Guidance literature:

With potassium hydroxide; potassium permanganate; In water; for 72h;

DOI:10.1021/jm00169a015

Reference yield: 73.0%

((3aS,4S,6S,6aS)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol → (3aR,4R,6S,6aS)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (72209-19-9)

Guidance literature:

((3aS,4S,6S,6aS)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol; With potassium permanganate; potassium hydroxide; In water; acetonitrile; at 20 ℃; for 20h;

With dihydrogen peroxide; In water; acetonitrile;

With hydrogenchloride; In water; pH=4;

DOI:10.1124/mol.116.105551

Reference yield:

2-Chloroadenosine (146-77-0) → 2-chloro-2',3'-O-isopropylideneadenosine-5'-carboxylic acid (72209-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / camphorsulfonic acid / acetone / 16 h / Ambient temperature

2: 74 percent / aq. KOH, KMnO₄ / H₂O / 72 h

With potassium hydroxide; potassium permanganate; camphor-10-sulfonic acid; In water; acetone;

DOI:10.1021/jm00169a015

upstream raw materials:

(2S,3S,4R,5S)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

2-Chloroadenosine

Downstream raw materials:

2-chloro-2',3'-O-isopropylideneadenosine-5'-N-ethylcarboxamide

(2S,3S,4R,5R)-5-(6-Amino-2-phenethylamino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methylamide

(3aS,4S,6R,6aR)-6-(6-Amino-2-phenethylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide

(3aS,4S,6R,6aR)-6-(6-Amino-2-benzylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide

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