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Please login or sign up for a free trial to access the full content. Method 4: From 5-Aminoimidazole-4-carbonitrile Riboside or 2′-Deoxyriboside

DOI: 10.1055/sos-SD-016-01192

Seela, F.; Ramzaeva, N.; Rosemeyer, H.Science of Synthesis, (200416989.

Nucleobase anion glycosylation of 6-substituted purines yields the N9-nucleosides as the main product. The situation changes if 5-aminoimidazole-4-carbonitrile is used instead of a purine as the precursor; then the main product is 4-amino-1-(ribofuranosyl)-1H-imidazole-5-carbonitrile (AICN-riboside) which is an intermediate in the synthesis of N7-glycosylated purines. Thus, facile conversion of acetylated 4-amino-1-(β-D-ribofuranosyl)-1H-imidazole-5-carbonitrile into 7-ribosylpurine-6-thione 78 is accomplished with diethoxymethyl acetate and hydrogen sulfide in pyridine (Scheme 50).[‌252‌]

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8-(8,8,8-Mee-M-eeeeee-β-M-eeeeeeeeeeeee)-8,8-eeeeeeeeeeeeee ee eeeeeeee ee eeee eeeeeee ee ee eeeeeeeee eeeeeeeeee eeee eeeeee eeeeeeeee ee eeeeeeee.[‌888‌] Meeeeeeeeeee ee 8-eeeee-8-(8-eeeee-β-M-eeeeeeeeeeeee)-8M-eeeeeeeee-8-eeeeeeeeeeee eeee eeeeeeeeeeeeee eeeeeee ee eeeeeeee ee eee eeeeeeeee ee 8-eeeeeeeeeeeeee; eeeeeeee eee eeeeeeee 8-eeeee-8-(8-eeeee-β-M-eeeeeeeeeeeee)-8M-eeeeeeeee-8-eeeeeeeeeeee eeeee eee M8-eeeeeeeeeeee eeeeee ee 8-eeeeeeeeeeeeee 88 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee 8-(8-Meeee-β-M-eeeeeeeeeeeee)eeeeeee[‌888‌]

Mee eeeeeeee ee eeeeeeeeeee eeeee eee eeeeee eeeeeeeeeee eeee eeeeeeeee 8-eeeee-8M-eeeeeeeee-8-eeeeeeeeeeee eeeeeeeeee, eeeeeeee ee eeeeeeeeeee eee eeeeeeeeeeee, eeeeeeee eeeeee eeeeee ee 8-eeeee eee 8-eeeeee eeeeeeeeeee ee eeeeeeeeeeee.[‌888‌] 8-Meeeeeeeeeeeeeeee (88) ee eeee eeeeeeeeeee eeee eee eeee eeeeeeeee eeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-(β-M-Meeeeeeeeeeee)-8-eeeeeeeeeeeeeeee (88):[‌888‌]

8-Meeee-8-(8,8,8-eee-M-eeeeee-β-M-eeeeeeeeeeeee)-8M-eeeeeeeee-8-eeeeeeeeeeee (8.8e, 8.8eeee) eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee (88eM) eee 8e eee eee eeeeee eeee eee eeee eeeeeeeeee ee eeeee ee eeee e eeeee. Meee eeeee eee eeeeeeeee ee eeeeeeee (888eM) eee eeeeeeee eeeeee M8M(e) eee eeeeee eeeeeee eeeeeee eee eeee eee 8e. Mee eeee eee eeee eeeeeeee eeeeeee eeeeeeee ee M8M eee ee eeeeeeeeee 88e. Mee eeee eeee eee eeeeeeeeee ee eeeee, eee eeee eeeeeee eeee MeMM (888eM) eeee eee eeeeeeeeee eeee eeeeeeeee eeee MM8. Meee eeeeeee eee eeeeeee ee eeeee eee 88e ee ee eee eeee eeeeeeeeee ee eeeee ee eeee e eeeeeeeee. Mee eeeeeeeee eee eeeeeeeee ee M8M (88eM), eee eM eeeeeeee ee 8 eeee eeeee ee MMe, eee eee eeee eee eeeeeee ee eeeee ee ee eee 8e. Mee eeeeeeeeeee eee eeeeeeee; eeeee: 8.88e (88%); ee 888888°M.

8-(8-Meeee-β-M-eeeeeeeeeeeee)eeeeeee (88):[‌888‌]

M eeee ee 8-eeeee-8-[8-eeeee-8,8-ee-M-(8-eeeeeee)-β-M-eeeeeeeeeeeee]-8M-eeeeeeeee-8-eeeeeeeeeeee (888ee, 8.88eeee) ee eeeeeeeeeeeeee eeeeeee (88eM) eee eeeeeeee eee 8e. Mee eeee eee eeeeeeeeee, eee eeeeeeeee eeeee eeeeeeeee ee eeeeeee, eee eeeee eeeeeeeeee. Meeeeeeeee MM8 (88eM, eeeeeeeeee eeeeeeeee ee 8°M) eee eeeee eee eee eeee eee eeeeeee ee ee eee 88e. Meeee eeeeeeeeeee, eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee 88 M, MM8Me8/MeMM 8:8). Meeee eeeeeeeeeeeeeee (MeMM), eeeeeeeee eeeeeeee eeee eeeeeeee; eeeee: 888ee (88%); ee 888°M.

8-Meeeeeeeeeeeeeeee (88):[‌88‌]

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