CID 14209051

Base Information

• Chemical Name: CID 14209051
• CAS No.: 26929-65-7
• Molecular Formula: C9H11N5O5
• Molecular Weight: 269.217
• Hs Code.: 29349990
• European Community (EC) Number: 248-113-6
• Mol file: 26929-65-7.mol

Synonyms:2'-azido-2'-deoxyuridine

Chemical Property of CID 14209051

Chemical Property:

• Melting Point: 149-153 ºC
• PSA: 154.30000
• LogP: -2.08114
• Storage Temp.: 2-8°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 269.07601847
• Heavy Atom Count: 19
• Complexity: 474

Purity/Quality:

99% ^*data from raw suppliers

1-[3-Azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)N=[N+]=[N-]
• Isomeric SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@H]([C@H](O2)CO)O)N=[N+]=[N-]

Technology Process of CID 14209051

There total 5 articles about CID 14209051 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: 89.0%

2,2'-Anhydrouridine (3736-77-4) → 2'-azido-2'-deoxyuridine (26929-65-7)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; trimethylsilylazide; lithium fluoride; In N,N-dimethyl-formamide; at 105 ℃; for 48h;

DOI:10.1016/j.tetlet.2008.09.078

Reference yield:

uridine (58-96-8) → 2'-azido-2'-deoxyuridine (26929-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: bis(phenyl) carbonate / N,N-dimethyl-formamide / 80 °C

1.2: 115 °C

2.1: N,N,N,N,-tetramethylethylenediamine; trimethylsilylazide; lithium fluoride / N,N-dimethyl-formamide / Heating

With bis(phenyl) carbonate; N,N,N,N,-tetramethylethylenediamine; trimethylsilylazide; lithium fluoride; In N,N-dimethyl-formamide;

DOI:10.1021/ja1048169

Reference yield:

2,2'-anhydro-3',5'-di-O-pivaloyluridine (38642-36-3) → 2'-azido-2'-deoxyuridine (26929-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonia / methanol / 3 h / 0 - 20 °C

2: lithium azide / N,N-dimethyl-formamide / 18 h / 135 °C

With lithium azide; ammonia; In methanol; N,N-dimethyl-formamide;

DOI:10.1080/15257770.2016.1188943

upstream raw materials:

2,2'-Anhydrouridine

uridine

2,2'-anhydro-3',5'-di-O-pivaloyluridine

2',3'-O-sulfinyl uridine

Downstream raw materials:

2′-azido-2′-deoxycytidine

2'-deoxy-2'-(3-methoxybenzamido)uridine

2,-deoxy-2'-(2-furyl-2-ethoxycarbonylamino)-5'-O-(4,4'-dimethoxytrityl)uridine

C₃₆H₃₆N₄O₉

Refernces

• 1、 McGee,Vargeese,Zhai,Kirschenheuter,Settle,Siedem,Pieken. "Efficient synthesis of 2'-amino-2'-deoxypyrimidine 5'- triphosphates". . p. 1329 - 1339. Retrieved 1995.
• 2、 Torrence,Waters,Witkop. "Unexpected conformational stability of poly(2'-azido-2'-deoxyuridylic acid).". . p. 3638 - 3639. Retrieved 1972.
• 3、 Ivanov, Andrei A.,Ko, Hyojin,Cosyn, Liesbet,Maddileti, Savitri,Besada, Pedro,Fricks, Ingrid,Costanzi, Stefano,Harden, T. Kendall,Van Calenbergh, Serge,Jacobson, Kenneth A.. "Molecular modeling of the human P2Y2 receptor and design of a selective agonist, 2′-amino-2′-deoxy-2-thiouridine 5′-triphosphate". . p. 1166 - 1176. Retrieved 2007.
• 4、 Szlenkier, Maurycy,Kamel, Karol,Boryski, Jerzy. "Regioselective Mitsunobu Reaction of Partially Protected Uridine". . p. 410 - 425. Retrieved 2016/08/05.