3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-aldehydo-D-glycero-D-ido-heptose | 652993-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-aldehydo-D-glycero-D-ido-heptose
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-formyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 652993-93-6
• 化学式: C₃₀H₃₃NO₆
• 分子量: 503.595
• InChiKey: PINLKVSXDWNCOC-CMPUJJQDSA-N

物化性质

• 沸点：
  689.9±55.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-aldehydo-D-glycero-D-ido-heptose 在 sodium tetrahydroborate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 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 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-aldehydo-D-glycero-D-ido-heptose
  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 <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.