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- W2951868984 abstract "The preparation of methyl (6R)-(6-2H1)-2-deoxy-2-N-acetamido-α-d-glucose (8α-d) and methyl (6R)-(6-2H1)-2-deoxy-2-N-acetamido-β-d-glucose (8β-d) is described. The key step in the synthesis was the stereoselective reduction of a C6-aldehydo-GlcNAc derivative with (R)-(+)-Alpine-Borane-d. Reduction of either methyl 6-aldehydo-3,4-di-O-benzyl-α-GlcNAc (6α) or methyl 6-aldehydo-3,4-di-O-benzyl-β-GlcNAc (6β) using (R)-(+)-Alpine-Borane-d in CH2Cl2 was significantly more stereoselective (>15:1 stereoselectivity for both anomers) than was reduction with NaBD4 in MeOH. The absolute stereochemistry at C6 of the deuterated GlcNAc derivatives was determined from 1H NMR analysis of the conformationally locked sugars, methyl (6R)-(6-2H1)-4,6-O-benzylidene-2-deoxy-2-N-acetamido-α-d-glucose (9α-d) and methyl (6R)-(6-2H1)-4,6-O-benzylidene-2-deoxy-2-N-acetamido-β-d-glucose (9β-d). Comparison of 3JH5,H6 values and 1H−1H NOEs for the nondeuterated and deuterated benzylidene derivatives showed that reduction with (R)-(+)-Al..." @default.
- W2951868984 created "2019-06-27" @default.
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- W2951868984 date "2010-06-18" @default.
- W2951868984 modified "2023-09-26" @default.
- W2951868984 title "ChemInform Abstract: Stereoselective Preparation of Deuterium-Labeled Sugars: (6R)-(6-2H1)-N-Acetylglucosamine Derivatives." @default.
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- W2951868984 doi "https://doi.org/10.1002/chin.199850247" @default.
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