3'-azido-2',3'-dideoxy-5-iodouridine

Base Information

• Chemical Name: 3'-azido-2',3'-dideoxy-5-iodouridine
• CAS No.: 85236-92-6
• Molecular Formula: C9H10 I N5 O4
• Molecular Weight: 379.11127
• Mol file: 85236-92-6.mol

Synonyms:3'-Azido-2',3'-dideoxy-5-iodouridine

Chemical Property of 3'-azido-2',3'-dideoxy-5-iodouridine

Chemical Property:

• PSA: 134.33000
• LogP: -0.03504

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3'-azido-2',3'-dideoxy-5-iodouridine

There total 8 articles about 3'-azido-2',3'-dideoxy-5-iodouridine 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: 83.0%

1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-iodouracil (87190-83-8) → 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-iodouracil (85236-92-6)

Guidance literature:

In acetic acid; at 100 ℃;

Reference yield: 36.0%

1-(3-chloro-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione (85236-91-5) → 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-iodouracil (85236-92-6)

Guidance literature:

With lithium azide; In dimethyl sulfoxide; at 90 ℃; for 48h;

DOI:10.1021/jm00360a019

Reference yield:

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) → 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-iodouracil (85236-92-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / pyridine / CH₂Cl₂ / 288 h / 24 °C

2: triphenylphosphine, CCl₄ / N,N-dimethyl-acetamide

3: 61 percent / zinc bromide / CH₂Cl₂ / 24 °C

4: 36 percent / lithium azide / dimethylsulfoxide / 48 h / 90 °C

With pyridine; tetrachloromethane; lithium azide; triphenylphosphine; zinc dibromide; In dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide;

DOI:10.1021/jm00360a019

upstream raw materials:

Navuridine

1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-iodouracil

1-(3-chloro-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione

5-Iodo-2'-deoxyuridine

Downstream raw materials:

2,5'-anhydro-3'-azido-2',3'-dideoxy-5-iodouridine

1-((2R,4S,5S)-4-Azido-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

3'-azido-5'-O-(p-tolylsulfonyl)-2',3'-dideoxy-5-iodouridine

1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-iodouracil

Refernces

• 1、 Lin, Tai-Shun,Gao, You-Song,Mancini, William R.. "Synthesis and Biological Activity of Various 3'-Azido and 3'-Amino Analogues of 5-Substituted Pyrimidine Deoxyribonucleosides". . p. 1691 - 1696. Retrieved 2007/10/02.