3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-aldehydo-D-glycero-D-gulo-heptose | 652993-94-7

• 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-gulo-heptose
• 英文别名: 2-(N-acetyl)-2-deoxy-1-formyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside；N-[(2R,3R,4R,5S,6R)-2-formyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 652993-94-7
• 化学式: C₃₀H₃₃NO₆
• 分子量: 503.595
• InChiKey: PINLKVSXDWNCOC-PGVCKJCBSA-N

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-gulo-heptose 在 sodium chlorite 、 2-甲基-2-丁烯 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 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：

  1-(2'-acetamido-2'-deoxy-α-D-glucopyranosyl)-2-propene 在 (Ph₂Me)2IrCOD*PF₆ 、 sodium hydride 、 potassium carbonate 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 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-gulo-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

• A Short Synthetic Route to β-<i>C</i>-Glycosides of <i>N</i>-Acetylglucosamine
  作者：Stéphanie Norsikian、Stéphanie Rat

  DOI：10.1055/s-2006-939061

  日期：——

  A short and efficient process is described for the synthesis of protected and unprotected 1-formyl-C-glycosides of N-acetylglucosamine.

  本文介绍了一种简捷高效的合成 N-乙酰氨基葡萄糖受保护和未受保护的 1-甲酰基-C-糖苷的工艺。
• 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.
• New and general synthesis of β-C-glycosylformaldehydes from easily available β-C-glycosylpropanones
  作者：Stéphanie Norsikian、Jennifer Zeitouni、Stéphanie Rat、Sylvie Gérard、André Lubineau

  DOI：10.1016/j.carres.2007.09.002

  日期：2007.12

  A highly effective method for the introduction of a formyl group at the anomeric position of pyranosides was developed via enolisation Of beta-C-D-glycopyranosylpropan-2-one using thermodynamic conditions then oxidative cleavage of the more substituted double bond. This sequence affords the desired aldehydes that are conveniently protected as aminals for purification and storage and easily regenerated using Dowex resin H+. In this paper, the syntheses of nine differently protected aldehydes derived from D-glucose, D-galactose. lactose and N-acetyl-D-glucosamine are presented. Our strategy proved to be very efficient in most cases excepted in the D-mannose series. (C) 2007 Elsevier Ltd. All rights reserved.