Methyl-4-amino-4,6-dideoxy-α-L-mannopyranosid | 22594-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-4-amino-4,6-dideoxy-α-L-mannopyranosid
• 英文别名: (2R,3R,4R,5R,6S)-5-amino-2-methoxy-6-methyloxane-3,4-diol
• CAS: 22594-28-1
• 化学式: C₇H₁₅NO₄
• 分子量: 177.2
• InChiKey: ZKLOBJYVQKYNSP-PAMBMQIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-月桂酰甘氨酸 、 Methyl-4-amino-4,6-dideoxy-α-L-mannopyranosid 在 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 methyl 4-deoxy-4-(dodecanoylglycyl)amino-β-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin—is the mode of action by modification of N-linked glycoproteins?

  摘要：

  The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl alpha-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to be highly cytotoxic towards human myeloma cells with an IC50=120 nM, whereas the D-(-)-enantiomer 2b, based on a D-mannose structure, shows no significant cytotoxicity. The analogue 16, in which the nucleotide base fragment has been replaced by a simple methoxy group, has no cytotoxicity. Initial studies towards clarifying the mechanism of anti-cancer action of spicamycin analogues are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00240-2
• 作为产物：
  描述：

  methyl 6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 Methyl-4-amino-4,6-dideoxy-α-L-mannopyranosid
  参考文献：
  名称：

  Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin—is the mode of action by modification of N-linked glycoproteins?

  摘要：

  The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl alpha-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to be highly cytotoxic towards human myeloma cells with an IC50=120 nM, whereas the D-(-)-enantiomer 2b, based on a D-mannose structure, shows no significant cytotoxicity. The analogue 16, in which the nucleotide base fragment has been replaced by a simple methoxy group, has no cytotoxicity. Initial studies towards clarifying the mechanism of anti-cancer action of spicamycin analogues are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00240-2

文献信息

• Syntheses of the l-manno and some other analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1
  作者：Emmanuel Poirot、Xiaodong Zhang、Noel F. Whittaker、Pavol Kováč

  DOI：10.1016/s0008-6215(00)00265-2

  日期：2001.1

  Analogs of the methyl alpha -glycosides of the terminal residues of the O-specific polysaccharides (O-PS) of Vibrio cholerae O:1, serotype Inaba and Ogawa, have been prepared as probes to study their interaction with anti V. cholerae O:1 antibodies. They differ from the termini of the respective O-PSs in anomeric or absolute configuration of perosamine, position of the O-methyl group in D-perosamine, and nature of the N-acyl side chain. (C) 2001 Elsevier Science Ltd. All rights reserved.