139757-71-4

Upstream product

• 139757-69-0 1,2,3,4-tetra-O-acetyl-6-O-tosyl-L-gulopyranoside 
• 1025990-61-7 (R)-1-((2R,5R)-2-Hydroxymethyl-[1,3]oxathiolan-5-yl)-ethane-1,2-diol 
• 139757-70-3 2,3,4-tri-O-acetyl-1-bromo-6-O-tosyl-α-L-gulopyranoside 
• 160956-73-0 2,3,4-Tri-O-acetyl-1,6-thioanhydro-L-gulose 
• 139689-02-4 (-)-1,6-dideoxy-1,6-thioanhydro-L-gulose 
• 6619-07-4 Toluene-4-sulfonic acid (2S,3S,4S,5S)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 655-45-8 L-gulose 
• 1025959-81-2 tert-Butyl-[(2R,5R)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-ylmethoxy]-diphenyl-silane 
• 139689-03-5 [(2R,5R)-5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-yl]-methanol 

Downstream Products

• 148774-90-7 (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carbaldehyde 
• 139689-04-6 (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carboxylic acid 
• 324015-67-0 (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane 
• 145985-97-3 (2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>cytosine 
• 145985-98-4 (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>cytosine 
• 139757-74-7 (2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine 
• 139757-73-6 (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine 
• 145986-23-8 (+)-(2R,5R)-5-iodo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine 
• 145913-72-0 (-)-(2R,5S)-5-iodo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine 
• 145986-22-7 (+)-(2R,5R)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine 
• 145913-71-9 (-)-(2R,5S)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine 
• 145986-21-6 (+)-(2R,5R)-5-chloro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine 
• 145913-70-8 (-)-(2R,5S)-5-chloro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine 
• 145986-20-5 (+)-(2R,5R)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine 

Relevant academic research and scientific papers

Asymmetric Synthesis and Biological Evaluation of β-L-(2R,5S)- and α-L-(2R,5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides as Potential Anti-HIV Agents

In order to study the structure-acivity relationships of L-oxathiolanyl nucleosides as potential anti-HIV agents, a series of enantiomerically pure L-oxathiolanyl pyrimidine and purine nucleosides were synthesized and evaluated for anti-HIV-1 activity in human peripheral blood mononuclear (PBM) cells.The key intermediate 8 was synthesized starting from L-gulose via 1,6-thiaanhydro-L-gulopyranose.The acetate 8 was condensed with thymine, 5-substituted uracils and cytosines, 6-chloropurine, and 6-chloro-2-fluoropurine to give pyrimidine and purine nucleosides.Upon evaluation of these final nucleosides, the 5-fluorocytosine derivative 51 was found to be the most potent compound among those tested.In the case of 5-substituted cytosine analogues, the antiviral potency was found to be in the following decreasing order: cytosine (β-isomer) > 5-iodocytosine (β-isomer) > 5-fluorocytosine (α-isomer) > 5-methylcytosine (α-isomer) > 5-methylcytosine (β-isomer) > 5-bromocytosine (β-isomer) > 5-chlorocytosine (β-isomer).Among the thymine, uracil, and 5-substituted uracil derivatives, thymine (α-isomer) and uracil (β-isomer) derivatives exhibited moderate anti-HIV activity.In the purine series, the antiviral potency is found to be in the following decreasing order: adenine (β-isomer) > 6-chloropurine (β-isomer) > 6-chloropurine (α-isomer) > 2-NH2-6-Cl-purine (β-isomer) > guanine (β-isomer) > N6-methyladenine (α-isomer) > N6-methyladenine (β-isomer).The cytotoxicity was also determined in human PBM cells as well as Vero cells.None of the synthesized nucleosides was toxic up to 100 μ in PBM cells.