190970-11-7

Upstream product

• 114861-14-2 1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose 
• 190779-52-3 ethyl-3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-D-glucopyranoside 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 177412-79-2 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-4-yl ester 
• 30253-76-0 1,3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranoside 
• 75783-45-8 (3aR,5R,6aS)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 190970-10-6 1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose 

Downstream Products

• 190970-17-3 C₇₀H₇₁N₅O₁₅ 
• 190970-16-2 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester 
• 190970-14-0 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-3-yl ester 
• 190970-15-1 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5R)-4-acetoxy-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yloxy]-6-acetoxymethyl-tetrahydro-pyran-3-yl ester 
• 190970-12-8 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(3aR,5R,6R,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

An expeditious route to the synthesis of adenophostin A

Glycosylation of 1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose (8) with ethyl 3,4,6-tri-O-acetyl-2-O-1-thio-α/β-D-glucopyranoside (7) under the agency of N-iodosuccinimide and trifluoromethanesulfonic acid afforded α-linked dimer 10 in 95% yield. Acetylation of 13, obtained after hydrogenation of 10 followed by pivaloylation of 11 (→12) and deacetonation, yielded penta-acetate 14. Vorbruggen-type condensation of 14 with bis-trimethylsilyl 6-N-benzoyladenine (9) gave adenosyl glucoside 17. Deacetylation of 17 resulted in migration of the pivaloyl group from the 2'-OH to the 3'-OH of the glucosyl moiety (→18), giving access, after phosphorylation and deprotection, to adenophostin A analog 4 containing two (2'-4')-cis oriented phosphate groups. Vorbrugen-type condensation of 9 with 16, obtained by deacetonation of 10 and subsequent acetylation, gave adenosyl glucoside 22. Protective group manipulations followed by phosphorylation furnished, after deprotection, homogeneous adenophostin A (2) in a high overall yield.

An expeditious route to the synthesis of adenophostin A

Glycosylation of 1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose (8) with ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α/β-D-glucopyranoside (7) under the agency of N-iodosuccinimide and trifluoromethanesulfonic acid (cat.) afforded α-linked dimer 10 in 95% yield. Vorbruggen-type condensation of 12, obtained by deacetonation of 10 and subsequent acetylation, with bis-trimethylsilyl N6-benzoyl adenine gave adenosyl glucoside 13. Protective group manipulations followed by phosphorylation furnished, after deprotection, homogeneous 2 in high overall yield.