124288-82-0

Upstream product

• 33985-40-9 (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 
• 124288-74-0 1,1-dimethylethyl (S)-5-amino-2-<<(4-methylphenyl)sulfonyl>-amino>pentanoate 
• 124288-75-1 1,1-dimethylethyl (S)-5-nitro-2-<<(4-methylphenyl)sulfonyl>amino>pentanoate 
• 110414-90-9 α-N-tosyl-δ-N-carbobenzoxyornthine 
• 124288-73-9 1,1-dimethylethyl (S)-2-<<(4-methylphenyl)sulfonyl>-amino>-5-<<(phenylmethoxy)carbonyl>amino>pentanoate 
• 124288-78-4 1,1-dimethylethyl amino>-2,3-O-(1-methylethylidene)-β-D-ribo-dec-5-enofuranosid>uronates 
• 124288-77-3 1,1-dimethylethyl amino>-2,3-O-(1-methyl-ethylidene)-β-D-ribo-dec-5-enofuranosid>uronates 
• 124288-76-2 (S)-6-Hydroxy-6-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-nitro-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester 
• 124288-80-8 1,1-dimethylethyl amino>-2,3-O-(1-methylethylidene)-β-D-ribo-6-deculofuranosid>uronate 

Downstream Products

• 124288-83-1 1,1-dimethylethyl -9(S)-<<(4-methylphenyl)sulfonyl>amino>-2,3-O-(1-methylethylidene)-β-D-allo-decofuranosid>uronate 
• 124288-99-9 (2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic acid tert-butyl ester 
• 1052664-36-4 (2S,5S)-2-[Benzyl-(toluene-4-sulfonyl)-amino]-5-methyl-6-((2R,3S,4R)-3,4,5-trihydroxy-tetrahydro-furan-2-yl)-hexanoic acid tert-butyl ester 
• 160451-40-1 tert-Butyl 1-(9-adenyl)-9(S)-(benzylamino)-1,5,6,7,8,9-hexadeoxy-6(S)-methyl-β-D-ribo-decofuranuronate 
• 1053254-55-9 tert-Butyl -2,3-O-isopropylidene-6(S)-methyl-5,6,7,8,9-pentadeoxy-β-D-allo-decofuranosid>uronate 
• 160451-39-8 tert-Butyl 1-(9-adenyl)-9(S)-(benzylamino)-2,3-di-O-acetyl-1,5,6,7,8,9-hexadeoxy-6(S)-methyl-β-D-ribo-decofuranuronate 
• 160451-38-7 tert-Butyl 1-(9-adenyl)-9(S)--2,3-di-O-acetyl-1,5,6,7,8,9-hexadeoxy-6(S)-methyl-β-D-ribo-decofuranuronate 
• 160451-36-5 tert-Butyl <9(S)--6(S)-methyl-5,6,7,8,9-pentadeoxy-1,2,3-tri-O-acetyl>-β-D-ribo-decofuranuronate 
• 160451-34-3 tert-Butyl -2,3-O-isopropylidene-5,7,8,9-tetradeoxy-6(R)-O-(p-toluenesulfonyl)-β-D-allo-decofuranosid>uronate 
• 58944-73-3 sinefungin 
• 124288-85-3 1,1-dimethylethyl amino>-2,3-O-(1-methylethylidene)-β-D-ribo-decofuranosid>uronate 
• 124288-92-2 (2S,5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester 
• 124288-91-1 1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate 
• 124288-90-0 1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-2,3-di-O-acetyl-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate 

Relevant academic research and scientific papers

Syntheses of 6-deaminosinefungin and (S)-6-methyl-6-deaminosinefungin

The nucleosides S-adenosylmethionine (SAM, AdoMet) and S-adenosylhomocysteine (SAH, AdoHcy) are involved in a number of important enzyme systems. The direct or indirect inhibition of these enzymes is currently of high interest, particularly in the areas of antiviral and cell proliferation research. We report here the first chirospecific syntheses of 6(S)-methyl-6-deaminosinefungin (4) and 6-deaminosinefungin (5) which are analogues of SAM (1), SAH (2), and sinefungin (3). From ketone 6 (tert-butyl [methyl 2,3-O-isopropylidene-5,7,8,9-tetradeoxy-9(S)-[(p-toluenesulfonyl)amino -β-D-ribo-deculofuranosid]uronate), an intermediate in the sinefungin synthesis, the methylene derivative was prepared by using the tosylhydrazone-hydroboration method. Nucleoside formation with adenine and deprotection then led to 6-deaminosine fungin. For the synthesis of (S)-6-methyl-6-deaminosinefungin (4), ketone 6 was converted in four steps into the 6(S)-methyl derivative using a cuprate reagent. After the adenine was attached, an appropriate deprotection sequence yielded 4. Thus, 4 was synthesized in 11 stops from ketone 6 in an overall yield of 13%.

Stereoselective Synthesis and Absolute Stereochemistry of Sinefungin

Sinefungin has been synthesized from D-ribose, L-ornithine, and adenine.L-Ornithine was converted to its δ-nitro analogue 10, which was coupled to the ribose derived aldehyde 11 by a potassium fluoride catalyzed nitro-aldol reaction.The resulting nitro al