(4aR,6S,7R,8S,8aR)-2-phenyl-7-phenylmethoxy-6-[(2R,3R,4S,5R,6R)-4,5,6-tris(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol | 144674-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,6S,7R,8S,8aR)-2-phenyl-7-phenylmethoxy-6-[(2R,3R,4S,5R,6R)-4,5,6-tris(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 144674-61-3
• 化学式: C₅₄H₅₆O₁₁
• 分子量: 881.032
• InChiKey: NZJQXYKXDBRLPJ-ILNRDUIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  65
• 可旋转键数：
  19
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-(methoxycarbonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl diethyl phosphite 、 (4aR,6S,7R,8S,8aR)-2-phenyl-7-phenylmethoxy-6-[(2R,3R,4S,5R,6R)-4,5,6-tris(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以38%的产率得到
  参考文献：
  名称：

  Efficient sialylation with phosphite as leaving group

  摘要：

  DOI：

  10.1016/s0040-4039(00)60022-9

文献信息

• An efficient synthesis of the Lewis X (Lex) antigen family
  作者：Alexander Toepfer、Richard R. Schmidt

  DOI：10.1016/s0040-4039(00)79122-2

  日期：1992.9

  tert-Butyldimethylsilyl 2-azido-4,6-benzylidene-glucopyranoside 3 proved to be a versatile starting material for the synthesis of Lex trisaccharide building block 7. Transformation into glycosyl donor 8a and acceptor 9, respectively, led to all building blocks required for the extension to hexa-, nona-, and dodecasaccharides 8b–d; with lactose acceptor 13 the corresponding octa-, undeca-, and tetradecasaccharides

  叔丁基二甲基甲硅烷基2-叠氮基-4,6-亚苄基-吡喃葡萄糖苷3被证明是合成Le x三糖结构单元7的通用原料。分别转化为糖基供体8a和受体9导致了扩展到六糖，九糖和十二糖8b–d所需的所有结构单元；用乳糖受体13，得到相应的八糖，十一糖和十四糖15b-d。“叠氮基鞘氨醇糖基化程序”提供了二聚体，三聚体和四聚体Le x抗原1b-d。
• Toepfer, Alexander; Kinzy, Willy; Schmidt, Richard R., Liebigs Annalen der Chemie, 1994, # 5, p. 449 - 464
  作者：Toepfer, Alexander、Kinzy, Willy、Schmidt, Richard R.

  DOI：——

  日期：——
• Utility of glycosyl phosphites as glycosyl donors-fructofuranosyl and 2-deoxyhexopyranosyl phosphites in glycoside bond formation
  作者：Thomas Müller、Regine Schneider、Richard R. Schmidt

  DOI：10.1016/s0040-4039(00)76961-9

  日期：1994.7

  The discussion of the ease of generating glycosyl donor properties in the important sugar categories (aldoses, ketoses, deoxy sugars, sugar uronates, and 3-deoxy-2-glyculosonates) implies that phosphites of ketoses and deoxy sugars, respectively, should be valuable donors. This is exhibited for fructofuranosyl phosphite 2 and for 2-deoxyhexopyranosyl phosphites 14a,b which are readily available and generally provide disaccharides in high yields.
• Efficient sialylation with phosphite as leaving group
  作者：Thomas J. Martin、Richard R. Schmidt(rk)

  DOI：10.1016/s0040-4039(00)60022-9

  日期：1992.10