2-[(2R,3R,4R,5S,6R)-2-Benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxymethyl]-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester | 328937-27-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2R,3R,4R,5S,6R)-2-Benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxymethyl]-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl] 2-[[(2R,3R,4R,5S,6R)-3-(1,3-dioxoisoindol-2-yl)-5-hydroxy-2-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxymethyl]benzoate
• CAS: 328937-27-5
• 化学式: C₆₉H₆₅NO₁₃S
• 分子量: 1148.34
• InChiKey: OHHYPYCWWHLQIC-QHCFBRHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  84
• 可旋转键数：
  26
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  183
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-[(2R,3R,4R,5S,6R)-2-Benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxymethyl]-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 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 0.33h， 以67%的产率得到2-[(1S,3R,5R,6R,7S,8R,19R,20R,21R,23R)-10-oxo-6,7,21-tris(phenylmethoxy)-5,23-bis(phenylmethoxymethyl)-2,4,9,18,22-pentaoxatetracyclo[17.4.0.03,8.011,16]tricosa-11,13,15-trien-20-yl]isoindole-1,3-dione
  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：

  在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.08h， 生成 2-[(2R,3R,4R,5S,6R)-2-Benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxymethyl]-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester
  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