methyl 2,3,4-tri-O-benzyl-6-O-(3,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside | 183885-26-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-(3,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside
• 英文别名: Bn(-3)[Bn(-4)]Man(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Man1Me；(2S,3S,4R,5R,6R)-6-(hydroxymethyl)-2-[[(2R,3R,4S,5S,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 183885-26-9
• 化学式: C₄₈H₅₄O₁₁
• 分子量: 806.95
• InChiKey: UWSOPYSRLWZBHT-DAIHUPALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 、 methyl 2,3,4-tri-O-benzyl-6-O-(3,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 在 molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到methyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-(3,4-di-O-benzyl-α-D-mannopyranosyl)-(1->6)-(2,3,4-tri-O-benzyl-α-D-mannopyranoside)
  参考文献：
  名称：

  Studies on the synthesis of two tetrasaccharides and the reactivity difference between them

  摘要：

  Studies on the reactivity of two synthetic tetrasaccharides as glycosyl accepters showed that condensation of the methyl alpha-glycoside with a disaccharide donor afforded a hexasaccharide, but condensation of the methyl beta-glycoside with the disaccharide did not yield the corresponding hexasaccharide under the same conditions. A combination of theoretical results and 2D NMR indicated that the reactivity difference between the methyl alpha-glycoside and the methyl beta-glycoside was determined mainly by steric effects. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00169-9
• 作为产物：
  描述：

  2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl trichloroacetate 在 molecular sieve 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(3,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  碳水化合物的研究XX。糖基三氯乙酸酯作为糖基供体合成含乳糖胺的六糖

  摘要：

  稳定且易于获得的中间体O-糖基三氯乙酸酯，经酸处理后被活化为高反应性糖基供体，并与受体偶联，从而提供了具有高立体选择性的复合糖苷。

  DOI：

  10.1016/0040-4039(96)01989-2

文献信息

• Synthesis of Laminin Hexasaccharide Analogue
  作者：Xianglan Ding、Fanzuo Kong

  DOI：10.1080/07328309808007463

  日期：1998.8.1

  The synthesis of laminin hexasaccharide analogue di-O-[Gal-beta-(1-->4)-Glc-beta]-(1-->2)-(1-->6)-man-alpha-(1-->6)-man-alpha-Me derivative (1) was achieved with 1,2-anhydro-mannopyranose benzyl ether (3) as the key intermediate. Coupling of 3 with methyl 2,3,4-tri-O-benzyl-alpha-D-mannopyranoside (4) promoted by ZnCl2 gave methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (2a). Selective 6-O-debenzylation of 2b with ZnCl2-Ac2O-HOAc followed by coupling with acetobromolactopyranose afforded 1.
• Synthesis of tumor-associated saccharides via O-glycosyl trichloroacetic
  作者：Xiao-Xiang Zhu、Ping Yu Ding、Meng-Shen Cai

  DOI：10.1016/0957-4166(96)00373-4

  日期：1996.10

  The trichloroacetic method was employed to synthesize di- and hexa-saccharides. O-glycosyl trichloroacetic, a stable and readily obtained intermediate, was activated to give a highly reactive glycosyl donor upon treatment with acid and coupled with the acceptor to afford complex glycosides with high stereoselectivity and in good yield. Two free hexasaccharides will be used to explore the possible prevention of metastatic spread. Copyright (C) 1996 Published by Elsevier Science Ltd