5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine

Base Information

• Chemical Name: 5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine
• CAS No.: 68144-26-3
• Molecular Formula: C₂₀H₂₀N₈O₄
• Molecular Weight: 436.43
• Mol file: 68144-26-3.mol

Synonyms:5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine

Chemical Property of 5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine

There total 12 articles about 5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine 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: 84.0%

N6-benzoyl-2',3'-O-isopropylidene-5'-O-methylsulfonyladenosine (40653-96-1) → 5'-azido-5'-deoxy-N6-benzoyl-2',3'-O-isopropylidene adenosine (68144-26-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 45h;

DOI:10.1080/15257779508014657

Reference yield: 80.0%

N-6-benzoyl-2',3'-O-isopropylideneadenosine (39947-04-1) → 5'-azido-5'-deoxy-N6-benzoyl-2',3'-O-isopropylidene adenosine (68144-26-3)

Guidance literature:

With sodium azide; carbon tetrabromide; triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0968-0896(99)00192-3

Reference yield:

N6-benzoyl-5'-bromo-O2',O3'-isopropylidene-5'-deoxy-adenosine (68144-27-4) → 5'-azido-5'-deoxy-N6-benzoyl-2',3'-O-isopropylidene adenosine (68144-26-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 90 ℃; for 24h; Inert atmosphere;

DOI:10.3390/molecules19022434

upstream raw materials:

N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-methylsulfonyladenosine

N-6-benzoyl-2',3'-O-isopropylideneadenosine

N-benzoyladenosine

2,2-dimethoxy-propane

Downstream raw materials:

5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-2',3'-O-isopropylideneuridine-6-methyl-(6(1)->5'-N)-5'-amino-N6-benzoyl-5'-deoxy-2',3'-O-isopropylideneadenosine

5'-acetamido-5'-deoxy-N₆-benzoyl-2',3'-O-isopropylideneadenosine

1-(5'-deoxy-N⁶,N⁶-dibenzoyl-2',3'-O-isopropylidene adenosin-5'-yl)-2-methyl-3-phenylsulfonyl-isothiourea

1-(N⁶-benzoyl-5'-deoxy-adenosin-5'-yl)-2-methyl-3-phenylsulfonyl-isothiourea

Refernces

• 1、 Peterson, Theodore V.,Streamland, Tobin U. B.,Awad, Ahmed M.. "A tractable and efficient one-pot synthesis of 5′-azido-5′- deoxyribonucleosides". . p. 2434 - 2444. Retrieved 2014/03/21.
• 2、 Wang, Ting,Lee, Hyun Joo,Tosh, Dilip K.,Kim, Hea Ok,Pal, Shantanu,Choi, Sun,Lee, Yoonji,Moon, Hyung Ryong,Zhao, Long Xuan,Lee, Kang Man,Jeong, Lak Shin. "Design, synthesis, and molecular modeling studies of 5′-deoxy-5′-ureidoadenosine: 5′-ureido group as multiple hydrogen bonding donor in the active site of S-adenosylhomocysteine hydrolase". . p. 4456 - 4459. Retrieved 2008/02/10.