(E)-1-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene | 537031-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene
• 英文别名: N-[(2R,3S,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[(E)-prop-1-enyl]oxan-3-yl]acetamide
• CAS: 537031-63-3
• 化学式: C₃₂H₃₇NO₅
• 分子量: 515.649
• InChiKey: QQOYUASBCMRJQT-WBMHHXGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 48.0h， 生成 dibenzyl (3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-ido-heptitol-1-yl) phosphate
  参考文献：
  名称：

  Synthesis of C‐Glycosyl Phosphate and Phosphonate, Analogues of N‐Acetyl‐α‐d‐Glucosamine 1‐Phosphate

  摘要：

  Synthesis of alpha-C-ethylene phosphate and phosphonate as well as alpha-C-methylene phosphate analogues of N-acetyl-alpha-D-glucosamine I-phosphate is reported starting from the common perbenzylated 2-acetamido-2-deoxy-alpha-C-allyl glucoside. Anomerisation of the corresponding amino alpha-C-glucosyl aldehyde to the beta-aldehyde was observed. Thus, both amino alpha- and beta-C-glucosyl methanol were obtained after reduction.

  DOI：

  10.1081/car-120026465
• 作为产物：
  描述：

  1-(2'-acetamido-2'-deoxy-α-D-glucopyranosyl)-2-propene 在 (Ph₂Me)2IrCOD*PF₆ 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (E)-1-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene
  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

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。
• The preparation of C-glycosyl amino acids—an examination of olefin cross-metathesis
  作者：Frank W. Schmidtmann、Tyler E. Benedum、Glenn J. McGarvey

  DOI：10.1016/j.tetlet.2005.04.110

  日期：2005.7

  A study investigating the structural features directing olefin cross-metathesis to afford C-glycoamino acids was carried out. These results lead to an appreciation of the importance of proximal functionality to the relative reactivity of olefins in metathesis reactions providing a variable that is useful to suppress undesirable self-metathesis. (c) 2005 Elsevier Ltd. All rights reserved.
• Development of Co- and Post-Translational Synthetic Strategies to <i>C</i>-Neoglycopeptides
  作者：Glenn J. McGarvey、Tyler E. Benedum、Frank W. Schmidtmann

  DOI：10.1021/ol0264861

  日期：2002.10.1

  [GRAPHICS]The synthesis of stable, C-linked analogues of glycopeptides is being investigated with two complementary synthetic strategies, co-translational and post-translational glycopeptide synthesis. The key feature of the present approach lies in an effective olefin cross-metathesis reaction that allows formation of both glycoamino acids and glycopeptides.
• Synthesis of <i>C</i>‐Glycosyl Phosphate and Phosphonate, Analogues of <i>N</i>‐Acetyl‐α‐<scp>d</scp>‐Glucosamine 1‐Phosphate
  作者：Olivier Gaurat、Juan Xie、Jean‐Marc Valéry

  DOI：10.1081/car-120026465

  日期：2003.12.31

  Synthesis of alpha-C-ethylene phosphate and phosphonate as well as alpha-C-methylene phosphate analogues of N-acetyl-alpha-D-glucosamine I-phosphate is reported starting from the common perbenzylated 2-acetamido-2-deoxy-alpha-C-allyl glucoside. Anomerisation of the corresponding amino alpha-C-glucosyl aldehyde to the beta-aldehyde was observed. Thus, both amino alpha- and beta-C-glucosyl methanol were obtained after reduction.
• 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.