[3-Azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate

Base Information

• Chemical Name: [3-Azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS No.: 106060-78-0
• Molecular Formula: C17H17 N5 O5
• Molecular Weight: 371.352
• DSSTox Substance ID: DTXSID40561084
• Mol file: 106060-78-0.mol

Synonyms:106060-78-0;[3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate;DTXSID40561084;5-O-BENZOYL-3-AZIDO-3-DEOXYTHYMIDINE;1-(3-Azido-5-O-benzoyl-2,3-dideoxypentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione;[(2R,3R,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl benzoate;[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl benzoate;132979-42-1

Chemical Property of [3-Azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 140.14000
• Density: g/cm³
• LogP: 1.12116
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 371.12296866
• Heavy Atom Count: 27
• Complexity: 696

Purity/Quality:

97% ^*data from raw suppliers

3'-AZIDO-5'-O-BENZOYL-3'-DEOXYTHYMIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)COC(=O)C3=CC=CC=C3)N=[N+]=[N-]

Technology Process of [3-Azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate

There total 13 articles about [3-Azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate 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: 90.0%

3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2) + benzoyl chloride (98-88-4) → 3'-azido-5'-O-benzoyl-3'-deoxythymidine (106060-78-0)

Guidance literature:

With pyridine; for 18h; Ambient temperature;

DOI:10.1021/jm00164a063

Reference yield: 82.0%

((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl benzoate (165047-02-9) → 3'-azido-5'-O-benzoyl-3'-deoxythymidine (106060-78-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 125 ℃; for 5h;

DOI:10.1016/0040-4039(95)01753-5

Reference yield: 80.0%

3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2) + benzoic acid anhydride (93-97-0) → 3'-azido-5'-O-benzoyl-3'-deoxythymidine (106060-78-0)

Guidance literature:

With dmap; In pyridine; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81755-5

upstream raw materials:

3'-azido-2',3'-deoxythymidine

benzoyl chloride

benzoic acid anhydride

2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine

Downstream raw materials:

3'-azido-2',3'-deoxythymidine

C₂₁H₂₃N₅O₆

C₂₀H₂₁N₅O₆

C₂₂H₂₅N₉O₄

Refernces

• 1、 Taourirte,Lazrek,Vasseur,Ferrero,Fernandez,Gotor. "Synthesis of new homo and heterodinucleosides containing the 2′,3′-dideoxynucleosides AZT and D4T". . p. 959 - 962. Retrieved 2001.
• 2、 -. "Methyl ketone derivative, and preparation method and applications thereof". Paragraph 0039; 0040. . Retrieved 2017/08/28.