[(2S,3R,4S,5R,6R)-5-hydroxy-2-methoxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl] 3-[[(2S,3R,4S,5R,6R)-2-ethylsulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxymethyl]benzoate | 328937-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5R,6R)-5-hydroxy-2-methoxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl] 3-[[(2S,3R,4S,5R,6R)-2-ethylsulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxymethyl]benzoate
• CAS: 328937-38-8
• 化学式: C₅₈H₆₄O₁₂S
• 分子量: 985.205
• InChiKey: KOKPFOXUFHGEBO-HOGURPJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  71
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,5R,6R)-5-hydroxy-2-methoxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl] 3-[[(2S,3R,4S,5R,6R)-2-ethylsulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxymethyl]benzoate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以78%的产率得到(4S,5R,6S,8R,9R,11R,13R,14R,15S,16R)-6-methoxy-5,14,15-tris(phenylmethoxy)-8,13-bis(phenylmethoxymethyl)-3,7,10,12,17-pentaoxatetracyclo[17.3.1.04,9.011,16]tricosa-1(22),19(23),20-trien-2-one
  参考文献：
  名称：

  Prearranged glycosides. Part 14: Intramolecular glycosylation of non-symmetrically tethered glycosides

  摘要：

  Partially benzylated 1-thio-beta -D-glucopyranosides were tethered via position 2 to position 3 of methyl alpha -D-glucopyranosyl and benzyl 2-phthalimido-2-deoxy-beta -D-glucopyranosyl derivatives, respectively, by non-symmetrical o-, m-, and p-methylbenzoate linkers. Intramolecular glycosylation of these prearranged glycosides lead to the corresponding non-symmetrically tethered alpha-(1-->4)-linked disaccharides as the exclusive or main products. The tethers were regioselectively opened by transesterification affording isomeric disaccharide accepters which are susceptible for further elongation of the sugar chain at positions 3 and 2', respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02032-3
• 作为产物：
  描述：

  ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydride 、 sodium cyanoborohydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.58h， 生成 [(2S,3R,4S,5R,6R)-5-hydroxy-2-methoxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl] 3-[[(2S,3R,4S,5R,6R)-2-ethylsulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxymethyl]benzoate
  参考文献：
  名称：

  Prearranged glycosides. Part 14: Intramolecular glycosylation of non-symmetrically tethered glycosides

  摘要：

  Partially benzylated 1-thio-beta -D-glucopyranosides were tethered via position 2 to position 3 of methyl alpha -D-glucopyranosyl and benzyl 2-phthalimido-2-deoxy-beta -D-glucopyranosyl derivatives, respectively, by non-symmetrical o-, m-, and p-methylbenzoate linkers. Intramolecular glycosylation of these prearranged glycosides lead to the corresponding non-symmetrically tethered alpha-(1-->4)-linked disaccharides as the exclusive or main products. The tethers were regioselectively opened by transesterification affording isomeric disaccharide accepters which are susceptible for further elongation of the sugar chain at positions 3 and 2', respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02032-3

文献信息

• Prearranged glycosides. Part 14: Intramolecular glycosylation of non-symmetrically tethered glycosides
  作者：Thomas Ziegler、Gregor Lemanski、Jürgen Hürttlen

  DOI：10.1016/s0040-4039(00)02032-3

  日期：2001.1

  Partially benzylated 1-thio-beta -D-glucopyranosides were tethered via position 2 to position 3 of methyl alpha -D-glucopyranosyl and benzyl 2-phthalimido-2-deoxy-beta -D-glucopyranosyl derivatives, respectively, by non-symmetrical o-, m-, and p-methylbenzoate linkers. Intramolecular glycosylation of these prearranged glycosides lead to the corresponding non-symmetrically tethered alpha-(1-->4)-linked disaccharides as the exclusive or main products. The tethers were regioselectively opened by transesterification affording isomeric disaccharide accepters which are susceptible for further elongation of the sugar chain at positions 3 and 2', respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.