79356-74-4

Upstream product

• 79308-61-5 ((R)-4-Oxo-5-trityloxymethyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester 
• 22900-10-3 2-deoxy-D-ribose 
• 79308-56-8 ((4S,5R)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester 
• 76-83-5 trityl chloride 
• 79308-52-4 ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate 
• 79356-76-6 ((2R,5R)-4-Oxo-5-trityloxymethyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 124290-99-9 (4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,4-diol 
• 22900-10-3 2-deoxy-β-D-erythro-pentopyranose 
• 79308-40-0 ethyl 2,3,4-trideoxy-D-ribo-hept-2-enoate 
• 452-51-7 D-2-deoxyribose 

Downstream Products

• 79308-53-5 [(4R,5R)-4-Hydroxy-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid ethyl ester 
• 79308-61-5 ((R)-4-Oxo-5-trityloxymethyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester 
• 79308-58-0 [(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester 
• 79308-56-8 ((4R,5R)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester 
• 79356-76-6 ((2R,5R)-4-Oxo-5-trityloxymethyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester 
• 79356-78-8 ((2R,4R,5R)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester 
• 112066-01-0 ethyl 2-((2S,5S)-5-((trityloxy)methyl)-2,5-dihydrofuran-2-yl)acetate 
• 111975-57-6 ((R)-5-Trityloxymethyl-2,5-dihydro-furan-2-yl)-acetic acid ethyl ester 
• 111670-49-6 ethyl 7-O-(triphenylmethyl)-6(R),7-dihydroxy-2(E),4(Z)-heptadienoate 
• 111670-51-0 ethyl 7-O-(triphenylmethyl)-6(S),7-dihydroxy-2(E),4(Z)-heptadienoate 
• 111670-50-9 ethyl 6-O-benzoyl-7-O-(triphenylmethyl)-6(S),7-dihydroxy-2(E),4(Z)-heptadienoate 
• 331755-37-4 9-[4-((2S,4S,5R)-4-Methoxymethoxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-butyl]-6-vinyl-9H-purin-2-ylamine 
• 331755-36-3 Toluene-4-sulfonic acid 4-((2S,4S,5R)-4-methoxymethoxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-butyl ester 

Relevant academic research and scientific papers

Stereocontrolled Synthesis of a Possible Stereoisomer of Laurenidificin and a Formal Total Synthesis of (+)-Aplysiallene Featuring a Stereospecific Ring Contraction

We report a highly stereocontrolled total synthesis of one of the possible stereoisomers of laurenidificin. Highlights of the synthesis include the formation of the 2,6-dioxabicyclo[3.3.0]octane framework by a stereospecific bromolactonization-α-bromination-ring contraction sequence, followed by a stereoselective propargylation, an insertion of the Z-enyne side chain by a hydroindation/cross coupling reaction, and ethylation at C13 with an organocuprate reagent. While the synthetic compound was not identical to the natural product, the absolute stereochemistry of the natural product was proposed on the basis of NMR analyses. Moreover, a formal total synthesis of (+)-aplysiallene was achieved by extending the ring contraction strategy. (Chemical Equation Presented).

Selective cross-linking to the adenine of the TA interrupting site within the triple helix

The triplex-forming oligonucleotide incorporating the new nucleoside derivative (2) that connects the 2-amino-6-vinylpurine moiety to the 2-deoxyribose unit with an ethyl spacer has exhibited highly selective cross-linking reaction to the adenine of the TA interrupting site within the triple helix.

Selective reaction to a flipping cytidine of the duplex DNA mediated by triple helix formation

A new nucleoside derivative (2) with a butyl spacer between the sugar part and the 2-amino-6-vinylpurine motif has been synthesized. The triplex-forming oligodeoxynucleotide incorporating 2 has achieved strand- and cytidine-selective cross-linking reaction to the G-C target site mediated by triple helix formation. It has been suggested that 2 reacts with a flipping cytidine at the target site.