phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→3)-1-thio-β-D-glucopyranoside | 1293912-54-5

• 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: phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→3)-1-thio-β-D-glucopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-3)Glc(b)-SPh；[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-phenylsulfanyloxan-4-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1293912-54-5
• 化学式: C₄₆H₄₂O₁₄S
• 分子量: 850.897
• InChiKey: BLGLLDUYWBSVHV-QIVAMQDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  61
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  219
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→3)-1-thio-β-D-glucopyranoside 在 silver trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以70%的产率得到phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)]-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  未保护苯基 1-硫代糖基吡喃糖苷与苯基硼酸作为瞬时掩蔽基团的区域选择性糖基化

  摘要：

  描述了一个有用的协议，用于在未保护的糖基受体中对仲醇进行区域选择性糖基化。衍生自 D-葡萄糖、D-半乳糖、D-葡萄糖胺、L-鼠李糖和 L-岩藻糖的苯基 1-硫代吡喃糖苷用苯基硼酸处理以安装临时硼酸酯，然后用过苯甲酰化吡喃葡萄糖基进行 Koenigs-Knorr 糖基化或吡喃半乳糖基溴化物。与葡萄糖苷和半乳糖苷的 3-位偶联获得了良好的产率，但其他受体的产率较低。使用苯基 1-硫代-β-D-吡喃葡萄糖苷，也可以通过超臂硫代半乳糖苷供体实现偶联。来自葡萄糖-葡萄糖偶联的产物可以在 6 位进行第二次区域选择性糖基化。在半乳糖系列中，

  DOI：

  10.1002/ejoc.201300723
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸一水合物 、 sodium methylate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 20.0 ℃ 、2.27 kPa 条件下， 反应 6.0h， 生成 phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→3)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Preparation of tagged glucose as a key intermediate in the synthesis of branched oligosaccharides

  摘要：

  Tagged and activated D-glucose was introduced as a building block for branched oligosaccharides. This building block was the oligosaccharide branching point at which selectively the C-2 followed by the C-3 position can be glycosylated. After the activation of the C-1 position by oxidation of a thiophenyl group, the newly formed tagged oligosaccharide can be used as a glycoside donor. Synthetic procedures for the preparation of phthalimide-based tag molecules as well as tagged monosaccharides are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.149

文献信息

• Regioselective Glycosylation of Unprotected Phenyl 1-Thioglycopyranosides with Phenylboronic Acid as a Transient Masking Group
  作者：Thomas Hauch Fenger、Robert Madsen

  DOI：10.1002/ejoc.201300723

  日期：2013.9

  A useful protocol is described for the regioselective glycosylation of the secondary alcohols in unprotected glycosyl acceptors. Phenyl 1-thioglycopyranosides derived from D-glucose, D-galactose, D-glucosamine, L-rhamnose, and L-fucose were treated with phenylboronic acid to install a temporary boronic ester, and then submitted to a Koenigs–Knorr glycosylation with perbenzoylated glucopyranosyl or galactopyranosyl

  描述了一个有用的协议，用于在未保护的糖基受体中对仲醇进行区域选择性糖基化。衍生自 D-葡萄糖、D-半乳糖、D-葡萄糖胺、L-鼠李糖和 L-岩藻糖的苯基 1-硫代吡喃糖苷用苯基硼酸处理以安装临时硼酸酯，然后用过苯甲酰化吡喃葡萄糖基进行 Koenigs-Knorr 糖基化或吡喃半乳糖基溴化物。与葡萄糖苷和半乳糖苷的 3-位偶联获得了良好的产率，但其他受体的产率较低。使用苯基 1-硫代-β-D-吡喃葡萄糖苷，也可以通过超臂硫代半乳糖苷供体实现偶联。来自葡萄糖-葡萄糖偶联的产物可以在 6 位进行第二次区域选择性糖基化。在半乳糖系列中，
• Preparation of tagged glucose as a key intermediate in the synthesis of branched oligosaccharides
  作者：Sunil K. Upadhyay、Branko S. Jursic

  DOI：10.1016/j.tetlet.2011.01.149

  日期：2011.4

  Tagged and activated D-glucose was introduced as a building block for branched oligosaccharides. This building block was the oligosaccharide branching point at which selectively the C-2 followed by the C-3 position can be glycosylated. After the activation of the C-1 position by oxidation of a thiophenyl group, the newly formed tagged oligosaccharide can be used as a glycoside donor. Synthetic procedures for the preparation of phthalimide-based tag molecules as well as tagged monosaccharides are presented. (C) 2011 Elsevier Ltd. All rights reserved.