benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[4-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside-3-O-yl)-1,4-dioxobutyl]-α-D-glucopyranoside | 316188-18-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[4-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside-3-O-yl)-1,4-dioxobutyl]-α-D-glucopyranoside
• CAS: 316188-18-8
• 化学式: C₆₀H₆₂O₁₄S
• 分子量: 1039.21
• InChiKey: FCIVMDUDHDYPFK-VHOMFLPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.74
• 重原子数：
  75.0
• 可旋转键数：
  23.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  152.74
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[4-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside-3-O-yl)-1,4-dioxobutyl]-α-D-glucopyranoside 在 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 4 Angstroem MS 、 sodium methylate 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 24.0h， 生成 Benzoic acid (2S,3R,4S,5S,6R)-2-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4S,5S,6R)-3,5-bis-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  摘要：

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.

  DOI：

  10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u
• 作为产物：
  描述：

  ethyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 四丁基硫酸氢铵 、 sodium hydride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.5h， 生成 benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[4-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside-3-O-yl)-1,4-dioxobutyl]-α-D-glucopyranoside
  参考文献：
  名称：

  摘要：

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.

  DOI：

  10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u

文献信息

• Synthesis ofβ-Mannosides via Prearranged Glycosides
  作者：Thomas Ziegler、Gregor Lemanski

  DOI：10.1002/(sici)1521-3773(19981204)37:22<3129::aid-anie3129>3.0.co;2-8

  日期：1998.12.4

  The choice of activator is decisive for whether the α-(1→4)-linked disaccharide 2 α or the anomeric compound 2 β is formed from the prearranged glycoside 1. Other β-mannosylsaccharides can also be synthesized selectively by intramolecular glycosylation. Bn=benzyl, Bz=benzoyl, MeOTf= methyl trifluoromethanesulfonate, NIS=N-iodosuccinimide.