2'-O,3'-O-Isopropylidene-5'-deoxy-5'-azidoadenosine

Base Information

• Chemical Name: 2'-O,3'-O-Isopropylidene-5'-deoxy-5'-azidoadenosine
• CAS No.: 34245-48-2
• Molecular Formula: C13H17N8O3+
• Molecular Weight: 332.322
• Mol file: 34245-48-2.mol

Synonyms:2',3'-O-isopropylidene 5'-azido 5'-deoxy adenosine;9-((3aR,4R,6R,6aR)-6-azidomethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-ylamine;2'-O,3'-O-Isopropylidene-5'-azido-5'-deoxyadenosine;5'-azido-5'-deoxy-2',3'-O-isopropylidene-adenosine;5'-Azido-2'-O,3'-O-isopropylidene-5'-deoxyadenosine;5'-azido-2',3'-O-isopropylidene adenosine;2'-O,3'-O-Isopropylidene-5'-deoxy-5'-azidoadenosine;5'-deoxy-5'-azido-2',3'-O-isopropylidene adenosine;

Chemical Property of 2'-O,3'-O-Isopropylidene-5'-deoxy-5'-azidoadenosine

Chemical Property:

• Melting Point: 137-139 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 147.06000
• Density: g/cm³
• LogP: 1.17026

Purity/Quality:

99% ^*data from raw suppliers

5'-Azido-5'-deoxy-2',3'-O-isopropylideneadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-O,3'-O-Isopropylidene-5'-deoxy-5'-azidoadenosine

There total 14 articles about 2'-O,3'-O-Isopropylidene-5'-deoxy-5'-azidoadenosine 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: 100.0%

2',3'-isopropylidene adenosine (362-75-4) → 5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine (34245-48-2)

Guidance literature:

2',3'-isopropylidene adenosine; With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; at 20 ℃; for 4h; Inert atmosphere;

With sodium azide; 15-crown-5; In 1,4-dioxane; at 110 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.bmc.2009.07.071

Reference yield: 90.0%

5'-diphenylphosphate-5'-deoxy-2',3'-isopropylidene adenosine (78111-39-4) → 5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine (34245-48-2)

Guidance literature:

With sodium azide; 15-crown-5; tetra-(n-butyl)ammonium iodide; In 1,4-dioxane; for 5h; Heating;

DOI:10.1016/S0040-4039(01)00395-1

Reference yield: 90.0%

9-((3aR,4R,6S,6aS)-6-(chloromethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine (24514-56-5) → 5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine (34245-48-2)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide;

DOI:10.1039/c4ob01734j

upstream raw materials:

5'-azido-5'-deoxy-2',3'-O-isopropylideneadenosine N¹-oxide

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

((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate

5'-diphenylphosphate-5'-deoxy-2',3'-isopropylidene adenosine

Downstream raw materials:

5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine

5'-azido-5'-deoxyadenosine

tert-butyl (9-((3aR,4R,6R,6aR)-6-(azidomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate

tert-butyl 9-(((3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate