123533-12-0

Basic information

• Product Name: 3'-isocyano-3'-deoxythymidine
• Synonyms: 3'-isocyano-3'-deoxythymidine
• CAS NO: 123533-12-0
• Molecular Formula: C₁₁H₁₃N₃O₄
• Molecular Weight: 0
• Mol File: 123533-12-0.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 3'-isocyano-3'-deoxythymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-isocyano-3'-deoxythymidine(123533-12-0)
• EPA Substance Registry System: 3'-isocyano-3'-deoxythymidine(123533-12-0)

Safety Data

• Hazardous Substances Data: 123533-12-0(Hazardous Substances Data)

Upstream product

• 124288-70-6 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-isocyanothymidine 
• 132149-42-9 5'-O-Acetyl-3'-carbylamino-3'-deoxythymidine 
• 123533-06-2 3'-azido-3'-deoxy-5'-O-thexyldimethylsilylthymidine 
• 124355-25-5 3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine 
• 126441-73-4 3'-formamido-3'-deoxy-5'-formylthymidine 
• 52450-18-7 3'-amino-3'-deoxythymidine 
• 29706-84-1 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine 
• 123533-05-1 5'-O-(thexyldimethylsilyl)anhydrothymidine 
• 123533-04-0 Methanesulfonic acid (2R,3S,5R)-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 50-89-5 thymidine 
• 132149-41-8 5'-O-Acetyl-3'-formylamino-3'-deoxythymidine 
• 117383-85-4 5'-O-(t-butyldimethylsilyl)-2,3'-anhydro-1-(2'-deoxy-β-D-threo-pentofuranosyl)thymine 
• 40733-28-6 5'-tert-butyldimethylsilyloxy-2'-deoxythymidine 
• 120624-97-7 1-{(2R,4S,5S)-4-azido-5-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}tetrahydrofuran-2-yl}-5-methylpyrimidine-2,4(1H,3H)-dione 

Downstream Products

• 133446-11-4 cis-chloro(3'-isocyan-3'-desoxythymidine)bis(triphenylphosphane)platinum(II)-tetrafluoroborate 

Relevant articles and documents

Synthesis and evaluation of new 2',3'-dideoxynucleoside analogs as potential anti-AIDS and anti-herpes drugs

Based on the known structure-activity relationships for the active anti-HIV, a series of 3'-deoxy-3'-N-functionalized thymidine analogs has been synthesized from thymidine. Evaluation for inhibitory activity against human immunodeficiency virus (HIV) replication in CEM cells and against herpes simplex virus in MRC-5 cells is reported.

Synthesis, Antiretrovirus Effects, and Phosphorylation Kinetics of 3'-Isocyano-3'-deoxythymidine and 3'-Isocyano-2',3'-dideoxyuridine

The silylated AzddThd 5 and AzddUrd 6 prepared from 2,3'-anhydronucleoside derivatives 3 and 4 were transformed to formamides 7 and 8 by using the sequence RN3 -> RN=P(C6H5) -> RNHCHO.Formamides 7 and 8 were dehydrated to the protected 3'-isocyano derivatives 9 and 10; deblocking gave 11 and 12.Neither 3'-isocyano-3'-deoxythymidine (11) nor 3'-isocyano-2',3'-dideoxyuridine (12) showed anti-HIV activity at noncytotoxic concentrations. ddThd derivative 11 was considerably more toxic to MT-4 cells than ddUrd derivative 12; it also had a much greater affinity (Ki) forMT-4 cell dThd kinase than ddUrd derivative 12.Both compounds appear to be linear mixed-type inhibitors of MT-4 cell dThd kinase.

SYNTHESIS OF 3'SUBSTITUTED-2',3'-DIDEOXYNUCLEOSIDE ANALOGS AS POTENTIAL ANTI-AIDS DRUGS

3'-Amino-3'-deoxythymidine 9 was prepared in six steps and in 67percent overall yield from thymidine.Five derivatives of 9 and compound 17 were tested for their anti-HIV activity.