3,5-O-Ditoluoyl 6-Chloropurine-7-β-D-deoxyriboside

Base Information

• Chemical Name: 3,5-O-Ditoluoyl 6-Chloropurine-7-β-D-deoxyriboside
• CAS No.: 91713-51-8
• Molecular Formula: C₂₆H₂₃ClN₄O₅
• Molecular Weight: 506.945
• Mol file: 91713-51-8.mol

Synonyms:3,5-O-Ditoluoyl 6-Chloropurine-7-β-D-deoxyriboside;6-Chloro-7-[2-deoxy-3,5-bis-O-(4-Methylbenzoyl)-β-D-erythro-pentofuranosyl]-7H-purine

Chemical Property of 3,5-O-Ditoluoyl 6-Chloropurine-7-β-D-deoxyriboside

Chemical Property:

• Melting Point: 152-153 °C
• Boiling Point: 684.5±65.0 °C(Predicted)
• PKA: -0.31±0.30(Predicted)
• PSA: 105.43000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 4.46660
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate

Purity/Quality:

97% ^*data from raw suppliers

3,5-O-Ditoluoyl6-Chloropurine-7-β-D-deoxyriboside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Impurity formed during the preparation of purine deoxynucleoside DNA adducts.

Technology Process of 3,5-O-Ditoluoyl 6-Chloropurine-7-β-D-deoxyriboside

There total 4 articles about 3,5-O-Ditoluoyl 6-Chloropurine-7-β-D-deoxyriboside 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: 61.0%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 6-chloropurine (87-42-3) → 6-Chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine (91713-46-1) + 6-chloro-7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-7H-purine (91713-51-8)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1) acetonitrile, RT, 30 min; 2) acetonitrile, 18 h;

DOI:10.1002/jhet.5570250653

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → 6-chloro-7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-7H-purine (91713-51-8)

Guidance literature:

Multi-step reaction with 3 steps

1: (+/-)-10-camphorsulfonic acid

2: 38 percent / pyridine / Ambient temperature

3: 25 percent / 4 Angstroem molecular sieves / iodonium dicollidine perchlorate / acetonitrile / 2 h

With pyridine; 4 A molecular sieve; camphor-10-sulfonic acid; iodonium di(2,4,6-trimethylpyridine) perchlorate; In acetonitrile;

DOI:10.1021/jo00077a057

Reference yield:

(2R,3S)-2-Hydroxymethyl-5-pent-4-enyloxy-tetrahydro-furan-3-ol → 6-chloro-7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-7H-purine (91713-51-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 38 percent / pyridine / Ambient temperature

2: 25 percent / 4 Angstroem molecular sieves / iodonium dicollidine perchlorate / acetonitrile / 2 h

With pyridine; 4 A molecular sieve; iodonium di(2,4,6-trimethylpyridine) perchlorate; In acetonitrile;

DOI:10.1021/jo00077a057

upstream raw materials:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

6-chloropurine

D-2-deoxyribose

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