methyl 6-azido-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside | 147314-49-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-azido-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(azidomethyl)-4,5,6-trimethoxyoxan-3-ol
• CAS: 147314-49-6
• 化学式: C₉H₁₇N₃O₅
• 分子量: 247.251
• InChiKey: RETIVDMJSWIXCV-ZEBDFXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 6-azido-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside 在 三氟甲磺酸酐 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 methyl 4-benzylamino-4,6-dideoxy-2,3-di-O-methyl-6-(N'-phenyl)thioureido-α-D-galactopyranoside
  参考文献：
  名称：

  Preparation of new type of organocatalysts having a carbohydrate scaffold

  摘要：

  The synthesis of nine new, bifunctional organocatalysts having carbohydrate scaffolds has been accomplished. In these catalysts both of the catalytic amino and thiourea functions are directly attached to a carbohydrate core. The activities of the newly prepared catalysts were tested in a Michael addition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.12.026
• 作为产物：
  描述：

  methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside 在 sodium azide 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 methyl 6-azido-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Preparation of new type of organocatalysts having a carbohydrate scaffold

  摘要：

  The synthesis of nine new, bifunctional organocatalysts having carbohydrate scaffolds has been accomplished. In these catalysts both of the catalytic amino and thiourea functions are directly attached to a carbohydrate core. The activities of the newly prepared catalysts were tested in a Michael addition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.12.026

文献信息

• Diastereoselective reduction of chiral N-tosyl 2-Benzoyl-1,3-oxazines derived from D-glucose
  作者：Kwang-Youn Ko、Jong-Yek Park

  DOI：10.1016/s0040-4039(96)02311-8

  日期：1997.1

  Stereochemistry of reduction of the diastereomerically pure N-tosyl 2-benzoyl-1,3-oxazines prepared from D-glucose was investigated with various reducing agents. It was found that the stereochemical outcome is consistent with the Cram's chelation model where the ring oxygen atom is involved in chelation, not the tosyl oxygen as in the 5-membered oxazolidines.

  用各种还原剂研究了由D-葡萄糖制备的非对映体纯的N-甲苯磺酰基2-苯甲酰基-1,3-恶嗪还原的立体化学。发现立体化学结果与克拉姆的螯合模型一致，在该模型中，环氧原子参与了螯合，而不是如五元恶唑烷中的甲苯磺酰氧。
• Synthesis of unexpected six-membered imides by free-radical carbocyclisation on carbohydrate templates
  作者：Renata B. de Oliveira、José D. de Souza Filho、Maria Auxiliadora F. Prado、Marcos N. Eberlin、Eduardo C. Meurer、Leonardo S. Santos、Ricardo J. Alves

  DOI：10.1016/j.tet.2004.08.039

  日期：2004.10

  Free-radical reactions of amido-esters anchored to a carbohydrate derived from methyl alpha-D-glucopyranoside afforded unexpected six-membered cyclic imides. Their structures were elucidated by ESI-MS/MS and NMR spectral analyses, and a mechanism for the formation of these imides is proposed. (C) 2004 Elsevier Ltd. All rights reserved.
• Fuerstner, Alois; Baumgartner, Judith; Jumbam, Denis N., Journal of the Chemical Society. Perkin transactions I, 1993, # 1, p. 131 - 138
  作者：Fuerstner, Alois、Baumgartner, Judith、Jumbam, Denis N.

  DOI：——

  日期：——
• Preparation of new type of organocatalysts having a carbohydrate scaffold
  作者：Károly Ágoston、Péter Fügedi

  DOI：10.1016/j.carres.2013.12.026

  日期：2014.5

  The synthesis of nine new, bifunctional organocatalysts having carbohydrate scaffolds has been accomplished. In these catalysts both of the catalytic amino and thiourea functions are directly attached to a carbohydrate core. The activities of the newly prepared catalysts were tested in a Michael addition. (C) 2014 Elsevier Ltd. All rights reserved.