Methyl 2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranoside | 210832-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranoside
• 英文别名: (2R,3S,4S,5S,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-methoxy-3,5-bis(phenylmethoxy)oxan-4-ol
• CAS: 210832-77-2
• 化学式: C₃₇H₄₄O₆Si
• 分子量: 612.838
• InChiKey: UMIBJGSLQKMDQB-FMRHBUHZSA-N

物化性质

• 沸点：
  670.1±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranoside 在 吡啶 、 硼烷四氢呋喃络合物 、 二甲基亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 [(2R,3S,4R,5S,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-methoxy-3,5-bis(phenylmethoxy)oxan-4-yl]methanol
  参考文献：
  名称：

  Application of the Anomeric Samarium Route for the Convergent Synthesis of the C-Linked Trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man and the Disaccharides α-d-Man-(1→3)-d-Man and α-d-Man-(1→6)-d-Man

  摘要：

  Studies are reported on the assembly of the branched C-trisaccharide, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.

  DOI：

  10.1021/jo020339z
• 作为产物：
  描述：

  甲基2,4-二-O-苄基吡喃己糖苷 、 叔丁基二苯基氯硅烷 在 吡啶 作用下， 反应 12.0h， 以87%的产率得到Methyl 2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Depre, Dominique; Dueffels, Arno; Green, Luke G., Chemistry - A European Journal, 1999, vol. 5, # 11, p. 3326 - 3340

  摘要：

  DOI：

文献信息

• Synthesis of 5-Thiomannose-containing oligomannoside mimics: Binding abilities to concanavalin A
  作者：Hideya Yuasa、Satoru Matsuura、Hironobu Hashimoto

  DOI：10.1016/s0960-894x(98)00207-8

  日期：1998.6

  Dissociation constants for the binding of these mimics to concanavalin A (ConA) were determined by a fluorescence anisotropy inhibition assay. Comparison of these data with those of the natural oligomannosides and with a crystal structure of the trimannoside-ConA complex established that replacing a ring oxygen atom with a sulfur atom causes about 1 kcal/mol decrease in the binding free energy when the ring

  含5-硫代甘露糖的寡甘露糖苷模拟物，5SMan alpha（1,6）Man，5SMan alpha（1,3）Man，5SMan alpha（1,6）¿Man alpha（1,3）Man¿，Man alpha（1,6）合成了5SMan alpha（1,3）Man和5SMan alpha（1,6）5SMan alpha（1,3）Man。通过荧光各向异性抑制测定法确定这些模拟物与伴刀豆球蛋白A（ConA）结合的解离常数。将这些数据与天然低聚甘露糖苷的数据以及三甘露糖苷-ConA配合物的晶体结构进行比较，发现当识别出环氧时，用硫原子取代环氧原子会导致结合自由能降低约1 kcal / mol。氢键
• Grice, Peter; Ley, Steven V.; Pietruszka, Joerg, Angewandte Chemie, 1996, vol. 108, # 2, p. 206 - 208
  作者：Grice, Peter、Ley, Steven V.、Pietruszka, Joerg、Priepke, Henning W. M.

  DOI：——

  日期：——
• Depre, Dominique; Dueffels, Arno; Green, Luke G., Chemistry - A European Journal, 1999, vol. 5, # 11, p. 3326 - 3340
  作者：Depre, Dominique、Dueffels, Arno、Green, Luke G.、Lenz, Roman、Ley, Steven V.、Wong, Chi-Huey

  DOI：——

  日期：——
• Application of the Anomeric Samarium Route for the Convergent Synthesis of the <i>C</i>-Linked Trisaccharide α-<scp>d</scp>-Man-(1→3)-[α-<scp>d</scp>-Man-(1→6)]-<scp>d</scp>-Man and the Disaccharides α-<scp>d</scp>-Man-(1→3)-<scp>d</scp>-Man and α-<scp>d</scp>-Man-(1→6)-<scp>d</scp>-Man
  作者：Lise Munch Mikkelsen、Sussie Lerche Krintel、Jesús Jiménez-Barbero、Troels Skrydstrup

  DOI：10.1021/jo020339z

  日期：2002.9.1

  Studies are reported on the assembly of the branched C-trisaccharide, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.