(4-Methyl-5-oxo-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-10-yl)methyl benzoate

Base Information

• Chemical Name: (4-Methyl-5-oxo-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-10-yl)methyl benzoate
• CAS No.: 70838-44-7
• Molecular Formula: C17H16N2O5
• Molecular Weight: 328.324
• NSC Number: 733564
• DSSTox Substance ID: DTXSID10991096
• Mol file: 70838-44-7.mol

Synonyms:70838-44-7;5'-O-benzoyl-2,3'-anhydrothymidine;(4-Methyl-5-oxo-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-10-yl)methyl benzoate;2,5-Methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one,3-[(benzoyloxy)methyl]-2,3-dihydro-8-methyl-, (2R,3R,5R)-;Oprea1_347197;DTXSID10991096;[(1R,9R,10R)-4-Methyl-5-oxo-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-10-yl]methyl benzoate;NSC733564;NSC-733564;FT-0662589;(8-Methyl-9-oxo-2,3-dihydro-5H,9H-2,5-methanopyrimido[2,1-b][1,5,3]dioxazepin-3-yl)methyl benzoate;2,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one, 3-[(benzoyloxy)methyl]-2,3-dihydro-8-methyl-, (2R,3R,5R)-(CI)

Chemical Property of (4-Methyl-5-oxo-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-10-yl)methyl benzoate

Chemical Property:

• Appearance/Colour: Colourless solid
• Boiling Point: 472.4 °C at 760 mmHg
• Flash Point: 239.5 °C
• PSA: 79.65000
• Density: 1.48 g/cm³
• LogP: 1.45720
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 328.10592162
• Heavy Atom Count: 24
• Complexity: 608

Purity/Quality:

97% ^*data from raw suppliers

5''-O-Benzoyl-2,3''-anhydrothymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN2C3CC(C(O3)COC(=O)C4=CC=CC=C4)OC2=NC1=O
• Uses: An intermediate in the preparation of anti-HIV pharmaceuticals

Technology Process of (4-Methyl-5-oxo-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-10-yl)methyl benzoate

There total 4 articles about (4-Methyl-5-oxo-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-10-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: 86.0%

benzoic acid (65-85-0,8013-63-6) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine (70838-44-7)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1039/c39900000801

Reference yield:

5′-benzoyl-3′α-methanesulfonyl-2′α-bromothymidine (165047-01-8) → 2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine (70838-44-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In N,N-dimethyl-formamide; at 125 - 130 ℃; for 2.5h;

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

Reference yield:

((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) → 2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine (70838-44-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone;

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

upstream raw materials:

benzoic acid

thymidine

5′-benzoyl-3′α-methanesulfonyl-2′α-bromothymidine

((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl benzoate

Downstream raw materials:

5'-O-benzoyl-3'-(2-tetrazolyl)-2',3'-dideoxythymidine

3'-α-C-allenyl-5'-O-benzoyl-2',3'-dideoxythymidine

1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)thymine

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

Refernces

• 1、 Mavila, Sudheendran,Worrell, Brady T.,Culver, Heidi R.,Goldman, Trevor M.,Wang, Chen,Lim, Chern-Hooi,Domaille, Dylan W.,Pattanayak, Sankha,McBride, Matthew K.,Musgrave, Charles B.,Bowman, Christopher N.. "Dynamic and Responsive DNA-like Polymers". supporting information. p. 13594 - 13598. Retrieved 2018/10/24.
• 2、 Naimi, Ebrahim,Zhou, Aihua,Khalili, Panteha,Wiebe, Leonard I.,Balzarini, Jan,De Clercq, Erik,Knaus, Edward E.. "Synthesis of 3′- and 5′-nitrooxy pyrimidine nucleoside nitrate esters: "Nitric oxide donor" agents for evaluation as anticancer and antiviral agents". . p. 995 - 1004. Retrieved 2007/10/03.