France at the Crystal Palace

Mainardi, Patricia; Walton, Whitney

doi:10.1525/9780520912144

Cited by 39 publications

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“…Two syntheses of 2‘- C -β-methylguanosine have been reported in the literature, both involving glycosylation of purines with an appropriately protected 2‘- C -β-methylribose derivative. , In a 1968 patent, Walton described the synthesis of 2‘ -C -β-methylguanosine via the reaction of 2,3,5-tri -O- benzoyl-2 -C- methyl-β- d -ribofuranosyl chloride with chloromercuripurine. Preparation of the glycosylating agent required eight steps from 2,3- O -isopropylidene- d -glyceraldehyde and gave low overall yield. , Additionally, the yield and selectivity of the glycosylation reactions with this reagent were not disclosed.…”

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confidence: 99%

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Efficient Synthesis of 2‘-C-β-Methylguanosine

Piccirilli²

2006

J. Org. Chem.

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2'-beta-Methyl nucleosides have potential value as therapeutic agents and as nucleoside analogues for exploring RNA biology. Here we develop a strategy for efficient synthesis for 2'-C-beta-methylguanosine (3). Starting from 1,2,3,5-tetra-O-benzoyl-2-C-beta-methyl-d-ribofuranose (1) and N2-acetylguanine, we obtained the title compound in two steps (78% overall yield) with high stereoselectivity (beta/alpha > 99:1) and high regioselectivity (N9/N7 > 99:1). Extension of this strategy to the classic synthesis of guanosine also resulted in high stereoselectivity (beta/alpha = 99:1) and improved regioselectivity (N9/N7 = 97:3).

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confidence: 99%

“…Preparation of the glycosylating agent required eight steps from 2,3-O-isopropylidene-D-glyceraldehyde and gave low overall yield. 11,12 Additionally, the yield and selectivity of the glycosylation reactions with this reagent were not disclosed.…”

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confidence: 99%