CAS: 76155-50-5; (2R,3S,4R,5R,6R)-5-Acetamido-2-(Acetoxymethyl)-6-Ethoxytetrahydro-2H-Pyran-3,4-Diyl Diacetate

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2495-96-7 40592-88-9 7772-79-4

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CAS号2495-96-7 N-((2R,3R,4R,5S...

📜P-Methylphenyl 3,4,6-Tri-O-Acetyl-2-Deoxy-2-Phthalimido-1-Thio-β-D-Glucopyranoside置于吡啶,N-碘代丁二酰亚胺,2,4,6-三叔丁基吡啶,三乙酰氧基硼,三氟甲磺酸三甲基硅酯,氨,Sodium,一水合肼体系中,用 四氢呋喃,甲醇,二氯甲烷 作为反应溶剂,化学反应 56.0H,反应生成 乙基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖苷
参考文献:Comparing The Use Of 2-Methylenenapthyl,4-Methoxybenzyl,3,4-Dimethoxybenzyl And 2,4,6-Trimethoxybenzyl As N-h Protecting Groups For P-Tolyl 2-Acetamido-3,4,6-Tri-O-Acetyl-2-Deoxy-1-Thio-β-D-Glucosides
标题:Comparing The Use Of 2-Methylenenapthyl,4-Methoxybenzyl,3,4-Dimethoxybenzyl And 2,4,6-Trimethoxybenzyl As N-h Protecting Groups For P-Tolyl 2-Acetamido-3,4,6-Tri-O-Acetyl-2-Deoxy-1-Thio-β-D-Glucosides
摘要:A Hurdle In Glycosylation Reactions Of 2-Acetamido Glycosyl Donors Is The Formation Of A Stable And Unreactive Oxazoline That Decreases The Yield Of These Reactions Significantly. As An Effort To Prevent Oxazoline Formation During Glycosylation Reactions,We Protected The N-H Of The Acetamido Group Within A 2-Acetamido-2-Deoxy-1-Thio-Beta-D-Glucoside With One Of Four Different Protecting Groups. These Groups Were Either 2-Methylenenapthyl,4-Methoxybenzyl,3,4-Dimethoxybenzyl Or 2,4,6-Trimethoxybenzyl. The Resulting N-Alkylacetamides Were Then Used In Glycosylation Reactions With Ethanol As A Model Acceptor. We Observed That The Ethyl Glycosides Obtained In Each Case Were Obtained With Exclusive 3-Selectivity Without The Formation Of Oxazoline Sideproducts. The Resulting Products Were Then Used To Screen Conditions For Protecting Group Removal. (C) 2010 Elsevier Ltd. All Rights Reserved.
DOI:10.1016/j.Carres.2010.11.026