2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranose；(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• 化学式: C₄₆H₅₄O₁₁
• 分子量: 782.928
• InChiKey: OIGCVNUVBSVJER-MTRLBPRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2'-(benzyloxycarbonyl)benzyl α-D-mannopyranoside 在 palladium on activated charcoal 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 4 A molecular sieve 、 ammonium acetate 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Glycosylation with 2′-Carboxybenzyl Glycosides as Glycosyl Donors: Scope and Application to the Synthesis of a Tetrasaccharide

  摘要：

  2′-羧基苄基（CB）2,3,4,6-四-O-苄基-α-d-甘露吡喃糖苷（3）、CB 2,3,4,6-四-O-苄基-β-d-葡萄吡喃糖苷（4）和CB 2,3-二-O-苄基-4,6-O-苄叉-β-d-葡萄吡喃糖苷（5）作为糖基供体与各种糖基受体反应，以高产率提供了相应的二糖。目前的CB糖苷方法学成功应用于高效构建四糖41。

  DOI：

  10.1055/s-2003-40348

文献信息

• A new efficient glycosylation method employing glycosyl pentenoates and PhSeOTf
  作者：Tae Jin Choi、Ju Yuel Baek、Heung Bae Jeon、Kwan Soo Kim

  DOI：10.1016/j.tetlet.2006.10.158

  日期：2006.12

  The PhSeOTf promoted glycosylations of various glycosyl acceptors with mannosyl pentenoates and glucosyl pentenoates as glycosyl donors afforded corresponding disaccharides in high yields. And the present glycosyl pentenoates/PhSeOTf method showed that the complete α-selective mannosylation of secondary alcohol acceptors was achieved with 2,3,4,6-tetra-O-benzyl-d-mannopyranosyl pentenoate to give α-disaccharides

  PhSeOTf以甘露糖基戊烯酸酯和葡糖基戊烯酸酯促进各种糖基受体的糖基化，因为糖基供体以高收率提供了相应的二糖。目前的糖基戊烯酸酯/ PhSeOTf方法表明，用2,3,4,6-四-O-苄基-d-甘露吡喃糖基戊烯酸酯可以实现仲醇受体的完整α-选择性甘露糖基化反应，从而获得高收率的α-二糖。
• Glycosyl iodides are highly efficient donors under neutral conditions
  作者：Michael J. Hadd、Jacquelyn Gervay

  DOI：10.1016/s0008-6215(99)00146-9

  日期：1999.7

  Abstract Glycosyl iodides have been prepared and subjected to glycosylation under neutral conditions. The reactions are highly efficient, giving α glycosides even with sterically demanding glycosyl acceptors. Glucosyl iodides react with allyl alcohol slowest and require refluxing conditions. Galactosyl iodides are intermediate in reactivity, providing the allyl glycoside in 3 h at room temperature

  摘要制备了糖基碘化物并在中性条件下进行糖基化。该反应是高效的，即使具有空间上要求的糖基受体也能得到α糖苷。葡萄糖基碘与烯丙醇的反应最慢，需要回流条件。半乳糖基碘化物是反应性的中间产物，在室温下3小时内可提供烯丙基糖苷，而岩藻糖基碘化物的糖基化在相似条件下可在不到1小时内发生。用包括异头羟基在内的各种受体证明了反应的范围和局限性，得到了海藻糖类似物。在不存在C-2参与的情况下，只需将溶剂从苯改成乙腈就可以实现葡萄糖基碘化物的β-选择性糖基化。
• Synthesis and Glycosylation of a Series of 6-Mono-, Di-, and Trifluoro <i>S</i>-Phenyl 2,3,4-Tri-<i>O</i>-benzyl-thiorhamnopyranosides. Effect of the Fluorine Substituents on Glycosylation Stereoselectivity
  作者：David Crich、Olga Vinogradova

  DOI：10.1021/ja0730258

  日期：2007.9.1

  A series of 6-mono-, di-, and trifluoro analogs of S-phenyl 2,3,4-tri-O-benzyl-D- or L-thiorhamnopyranoside has been synthesized and used as donors in glycosylation reactions, with activation by the 1-benzenesulfinyl pipe ridine/triflic anhydride system. The stereochemical outcome of the glycosylation reactions was found to depend on the electron-withdrawing capability of the disarming substituent at the 6-position, i.e., on the number of fluorine atoms present. The results are explained with regard to the increased stability of the glycosyl triflates, shown to be intermediates in the reaction by low-temperature H-1 NMR experiments, with increased fluorine content.
• A new glycosylation strategy for the synthesis of mannopyranosides
  作者：Gurdial Singh、Hariprasad Vankayalapati

  DOI：10.1016/s0957-4166(99)00487-5

  日期：2000.1

  Activation of the anomeric centre of 1-O-2,3,4,6-tetra-O-benzyl-D-mannopyranos propane-1,3-diyl phosphate in the presence of trimethylsilyl triflate allowed the preparation of alpha- or beta-manno-linked glycosides. (C) 2000 Elsevier Science Ltd. All rights reserved.
• FRASER-REID, BERT;KONRADSSON, PETER;MOOTOO, DAVID R.;UDODONG, UKO, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 12, 823-825
  作者：FRASER-REID, BERT、KONRADSSON, PETER、MOOTOO, DAVID R.、UDODONG, UKO

  DOI：——

  日期：——