3-(2'-N-acetylamino-2'-deoxy-β-D-glucopyranosyl)-1-propene | 180778-41-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2'-N-acetylamino-2'-deoxy-β-D-glucopyranosyl)-1-propene
• 英文别名: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-prop-2-enyloxan-3-yl]acetamide
• CAS: 180778-41-0
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: PWFYUSQMOZEDLN-OGBGREFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2'-N-acetylamino-2'-deoxy-β-D-glucopyranosyl)-1-propene 在 sodium chlorite 、 sodium periodate 、 四氧化锇 、 2-甲基-2-丁烯 、 (Ph₂Me)2IrCOD*PF₆ 、 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 2.0h， 生成 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid
  参考文献：
  名称：

  Synthesis of α- and β-C-glycosides of N-acetylglucosamine

  摘要：

  As part of efforts to make available new, classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00818-9
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 偶氮二异丁腈 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 31.0h， 生成 3-(2'-N-acetylamino-2'-deoxy-β-D-glucopyranosyl)-1-propene
  参考文献：
  名称：

  Synthesis of β-C-Glycosides of N-Acetylglucosamine via Keck Allylation Directed by Neighboring Phthalimide Groups

  摘要：

  DOI：

  10.1021/jo960819o

文献信息

• Synthesis of new sugar amino acid derivatives of d-glucosamine
  作者：Juan Xie

  DOI：10.1016/s0008-6215(02)00487-1

  日期：2003.2

  The synthesis of several new sugar amino acid derivatives of 2-acetamido-2-deoxy-D-glucose, bearing a C-glycosyl functionality as building blocks for the design and synthesis of natural glycoconjugates mimetics, is described. These compounds were prepared from the readily accessible per-benzylated amino C-allyl glucopyranosyl compounds, with TMSOTf/Ac(2)O-mediated selective acetolysis of the 6-O-benzyl

  描述了几种新的2-乙酰氨基-2-脱氧-D-葡萄糖的糖氨基酸衍生物的合成，其带有C-糖基官能团，作为天然糖缀合物模拟物的设计和合成的基础。这些化合物是从容易获得的全苄基氨基C-烯丙基吡喃葡萄糖基化合物中制备的，其中TMSOTf / Ac（2）O介导的6-O-苄基的选择性乙酰水解是关键步骤。
• Synthesis of β-<i>C</i>-Glycosides of <i>N</i>-Acetylglucosamine via Keck Allylation Directed by Neighboring Phthalimide Groups
  作者：Barbara A. Roe、Constantine G. Boojamra、Jennifer L. Griggs、Carolyn R. Bertozzi

  DOI：10.1021/jo960819o

  日期：1996.1.1
• Synthesis of α- and β-C-glycosides of N-acetylglucosamine
  作者：Glenn J. McGarvey、Frank W. Schmidtmann、Tyler E. Benedum、Darin E. Kizer

  DOI：10.1016/s0040-4039(03)00818-9

  日期：2003.5

  As part of efforts to make available new, classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine. (C) 2003 Elsevier Science Ltd. All rights reserved.