(Methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl) isothiocyanate | 140933-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl) isothiocyanate
• 英文别名: (2R,3R,4S,5R,6S)-2-(isothiocyanatomethyl)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 140933-97-7
• 化学式: C₂₉H₃₁NO₅S
• 分子量: 505.635
• InChiKey: SKSYYHFUVMFSSB-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl) isothiocyanate 、 DL-(1,3/2,4,5)-5-amino-1-C-(hydroxymethyl)cyclopentane-1,2,3,4-tetraol 以 四氢呋喃 、 水 为溶剂， 反应 96.0h， 以88%的产率得到N-(Methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl)-N'-<<(1R)-(1α,2β,3α,4β,5β)>-1-(hydroxymethyl)-1,2,3,4-tetrahydroxycyclopent-5-yl>thiourea
  参考文献：
  名称：

  Syntheses of Trehazolin Derivatives and Evaluation as Glycosidase Inhibitors

  摘要：

  The trehazolin derivatives 9-12 were synthesized from the aminocyclitol (7), which is the degradation product of trehazolin (5). In particular, compounds 9-11 were pseudodisaccharides that underwent replacement of the corresponding nonreducing D-glucose moieties of isomaltose and maltose by trehalamine (6), and they were designed to be therapeutic drugs; however, they did not show significant activities.

  DOI：

  10.1021/jo00113a041
• 作为产物：
  描述：

  二硫化碳 、 methyl 6-deoxy-6-amino-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 生成 (Methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl) isothiocyanate
  参考文献：
  名称：

  Syntheses of Trehazolin Derivatives and Evaluation as Glycosidase Inhibitors

  摘要：

  The trehazolin derivatives 9-12 were synthesized from the aminocyclitol (7), which is the degradation product of trehazolin (5). In particular, compounds 9-11 were pseudodisaccharides that underwent replacement of the corresponding nonreducing D-glucose moieties of isomaltose and maltose by trehalamine (6), and they were designed to be therapeutic drugs; however, they did not show significant activities.

  DOI：

  10.1021/jo00113a041

文献信息

• Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides
  作者：Ian Cumpstey

  DOI：10.1016/j.carres.2009.09.008

  日期：2009.11

  This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioether or amine bridges to carbohydrates or other carbasugars.

  这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。
• Intramolecular amino delivery reactions for the synthesis of valienamine and analogues
  作者：Spencer Knapp、Andrew B.J. Naughton、T.G. Murali Dhar

  DOI：10.1016/s0040-4039(00)91850-1

  日期：1992.2

  Iodocyclization and [3,3] sigmatropic rearrangement reactions of N-substituted carbonimidothioates are used to prepare valienamine (1), 7-nor-valienamine (8), and the valienamine-based pseudo-disaccharide 12.
• Syntheses of Trehazolin Derivatives and Evaluation as Glycosidase Inhibitors
  作者：Yoshiyuki Kobayashi、Masao Shiozaki、Osamu Ando

  DOI：10.1021/jo00113a041

  日期：1995.4

  The trehazolin derivatives 9-12 were synthesized from the aminocyclitol (7), which is the degradation product of trehazolin (5). In particular, compounds 9-11 were pseudodisaccharides that underwent replacement of the corresponding nonreducing D-glucose moieties of isomaltose and maltose by trehalamine (6), and they were designed to be therapeutic drugs; however, they did not show significant activities.