3',5'-Di-O-acetyl O6-Benzyl-2'-deoxyguanosine

Base Information

• Chemical Name: 3',5'-Di-O-acetyl O6-Benzyl-2'-deoxyguanosine
• CAS No.: 144640-75-5
• Molecular Formula: C21H23N5O6
• Molecular Weight: 441.444
• Mol file: 144640-75-5.mol

Synonyms:[(2R,3S,5R)-3-acetyloxy-5-(2-amino-6-phenylmethoxypurin-9-yl)oxolan-2-yl]methyl acetate;

Chemical Property of 3',5'-Di-O-acetyl O6-Benzyl-2'-deoxyguanosine

Chemical Property:

• Boiling Point: 678.7±65.0 °C(Predicted)
• PKA: 2.93±0.10(Predicted)
• PSA: 141.41000
• Density: 1.48±0.1 g/cm3(Predicted)
• LogP: 1.69990
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

3’,5’-Di-O-acetylO6-Benzyl-2’-deoxyguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3',5'-Di-O-acetyl O6-Benzyl-2'-deoxyguanosine

There total 4 articles about 3',5'-Di-O-acetyl O6-Benzyl-2'-deoxyguanosine 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: 24.8%

3',5'-di-O-acetyl-2'-deoxyguanosine (69992-10-5) + benzyl alcohol (100-51-6,185532-71-2) → 3',5'-di-O-acetyl-O6-benzyl-2'-deoxyguanosine (144640-75-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; at 85 ℃; for 2h;

Reference yield: 24.8%

3’,5’-O-diacetyl-2’-deoxyguanosine (69992-10-5) + benzyl alcohol (100-51-6,185532-71-2) → 3',5'-di-O-acetyl-O6-benzyl-2'-deoxyguanosine (144640-75-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; at 85 ℃; for 2h;

DOI:10.1021/jm0493865

Reference yield:

2'-deoxyguanosine (961-07-9) → 3',5'-di-O-acetyl-O6-benzyl-2'-deoxyguanosine (144640-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / pyridine / 72 h / 20 °C

2: 24.8 percent / triphenylphosphine; diisopropylazodicarboxylate / dioxane / 2 h / 85 °C

With pyridine; di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; 2: Mitsunobu reaction;

DOI:10.1021/jm0493865

upstream raw materials:

3',5'-di-O-acetyl-2'-deoxyguanosine

benzyl alcohol

3’,5’-O-diacetyl-2’-deoxyguanosine

2'-deoxyguanosine

Downstream raw materials:

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-{6-benzyloxy-2-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-naphthalen-1-ylamino]-purin-9-yl}-tetrahydro-furan-3-yl ester

O⁶-benzyl-2-fluoro-2'-deoxyinosine

2-chloro-6-benzyloxy-9-[2'-deoxy-β-D-erythropentofuranosyl]purine diacetate

O⁶-Benzyl-2'-deoxyguanosine

Refernces

• 1、 Wei, Guangping,Loktionova, Natalia A.,Pegg, Anthony E.,Moschel, Robert C.. "β-Glucuronidase-cleavable prodrugs of O6-benzylguanine and O6-benzyl-2′-deoxyguanosine". . p. 256 - 261. Retrieved 2007/10/03.