3,5,6-tri-O-methyl-D-glucofuranose | 28436-51-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5,6-tri-O-methyl-D-glucofuranose
• 英文别名: 3,5,6-Tri-O-methyl-D-glucose；O³,O⁵,O⁶-trimethyl-D-glucose；(3R,4R,5R)-5-[(1R)-1,2-dimethoxyethyl]-4-methoxyoxolane-2,3-diol
• CAS: 28436-51-3
• 化学式: C₉H₁₈O₆
• 分子量: 222.238
• InChiKey: RDKAXOXIJSKPNU-VARJHODCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  15
• 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：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5,6-tri-O-methyl-D-glucofuranose 在 4-二甲氨基吡啶 、 sodium dihydrogenphosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3aS,5R,6S,6aR)-3-butanoyl-5-[(1R)-1,2-dimethoxyethyl]-6-methoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]oxazol-2-one
  参考文献：
  名称：

  New glyco-oxazolidin-2-ones as chiral auxiliaries in boron-mediated asymmetric aldol reactions

  摘要：

  Two new chiral glyco-oxazolidin-2-one auxiliaries based on D-glucose are described. Some N-acyl derivatives were synthesized and used in dialkylboron-mediated asymmetric aldol reactions. All reactions delivered as the major diastereomer those predicted by the Zimmerman-Traxler model and were separated by column chromatography and mostly isolated in moderate to good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00503-0
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 sodium hydroxide 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 3,5,6-tri-O-methyl-D-glucofuranose
  参考文献：
  名称：

  New glyco-oxazolidin-2-ones as chiral auxiliaries in boron-mediated asymmetric aldol reactions

  摘要：

  Two new chiral glyco-oxazolidin-2-one auxiliaries based on D-glucose are described. Some N-acyl derivatives were synthesized and used in dialkylboron-mediated asymmetric aldol reactions. All reactions delivered as the major diastereomer those predicted by the Zimmerman-Traxler model and were separated by column chromatography and mostly isolated in moderate to good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00503-0

文献信息

• Synthesis of <i>C</i>-Glycosyl Lactones and Protected <i>C</i>-Glycosyl Amino Acids:  Use of Radical Cyclization
  作者：Junhu Zhang、Derrick L. J. Clive

  DOI：10.1021/jo981435w

  日期：1999.2.1

  halogen on the adjacent carbon, were condensed with (2,2-diphenylhydrazono)acetic acid (2); the resulting esters undergo radical cyclization to afford carbohydrates fused to a 2,2-diphenylhydrazino lactone unit (6c,d-13c,d). In suitable cases (9c,d) such carbohydrate lactones can be elaborated into C-glycosyl amino acids.

  将保护的碳水化合物6a-13a与（2,2-二苯基肼基）乙酸（2）缩合，所述保护的碳水化合物6a-13a在相邻的碳上具有一个游离羟基和苯基硒烯基或卤素。所得酯进行自由基环化，得到与2，2-二苯基肼基内酯单元（6c，d-13c，d）融合的碳水化合物。在合适的情况下（9c，d），这种碳水化合物内酯可以被精加工成C-糖基氨基酸。
• Multi-Step Synthesis and Biological Evaluation of Analogues of Insulin Secretagogue (2S,3R,4S)-4-Hydroxyisoleucine
  作者：Kaïss Aouadi、Anne-Dominique Lajoix、René Gross、Jean-Pierre Praly

  DOI：10.1002/ejoc.200800744

  日期：——

  Synthetic analogues of (2S,3R,4S)‐4‐hydroxyisoleucine have been prepared, mainly from D‐glucose, by multi‐step syntheses and evaluated for their ability to induce insulin secretion in pancreatic β‐cells.

  （2 S，3 R，4 S）-4-羟基异亮氨酸的合成类似物主要是通过D-葡萄糖制备的，通过多步合成方法进行了合成，并评估了它们在胰腺β细胞中诱导胰岛素分泌的能力。
• Conformationally Restricted Chiral Peptide Nucleic Acids Derived from Azetidines
  作者：Lajos Kovács、Miklós Hornyák、Nicola M. Howarth

  DOI：10.1081/ncn-120022966

  日期：2003.10

  The initial experiments towards the chemical synthesis of conformationally rigid peptide nucleic acid analogues with azetidine moieties have been described.

  已经描述了化学合成具有氮杂环丁烷部分的构象刚性肽核酸类似物的初步实验。
• Just, George; Crosilla, Danilo, Canadian Journal of Chemistry, 1980, vol. 58, # 22, p. 2349 - 2357
  作者：Just, George、Crosilla, Danilo

  DOI：——

  日期：——
• Rumyantseva, S. A.; Sisneros, Ks.; Koroteev, M. P., Journal of general chemistry of the USSR, 1984, vol. 54, # 1, p. 181 - 185
  作者：Rumyantseva, S. A.、Sisneros, Ks.、Koroteev, M. P.、Nifant'ev, E. E.

  DOI：——

  日期：——