methyl (2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-β-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside | 69895-14-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-β-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
• 英文别名: Glc2Ac3Ac4Ac6Ac(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]a-Glc1Me；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-6-methoxy-2-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl] benzoate
• CAS: 69895-14-3
• 化学式: C₄₂H₄₄O₁₈
• 分子量: 836.801
• InChiKey: NBOGMAZIQQLGSI-RHZQRUEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  60
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl (2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-β-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 在 乙酰氯 作用下， 以 甲醇 为溶剂， 以92%的产率得到methyl β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of 1→6 Linked Manno-, Gluco-, and Galactopyranose Di-, Tri-, and Tetrasaccharides Via Orthoester Intermediates

  摘要：

  1-->6 Linked manno-, gluco-, and galactopyranose di-, tri-, and tetrasaccharides with 1,2-trans glycosidic linkages were concisely and effectively synthesized using peracetylated glycosyl bromides as the donors and unprotected or partially protected glycopyranosides as the accepters via orthoester intermediates.

  DOI：

  10.1080/07328300008544122
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 在 吡啶 、 2,4-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 methyl (2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-β-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of 1→6 Linked Manno-, Gluco-, and Galactopyranose Di-, Tri-, and Tetrasaccharides Via Orthoester Intermediates

  摘要：

  1-->6 Linked manno-, gluco-, and galactopyranose di-, tri-, and tetrasaccharides with 1,2-trans glycosidic linkages were concisely and effectively synthesized using peracetylated glycosyl bromides as the donors and unprotected or partially protected glycopyranosides as the accepters via orthoester intermediates.

  DOI：

  10.1080/07328300008544122

文献信息

• Glycosylation Reaction of <i>Thioglycosides</i> by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter
  作者：Tetsuya Kajimoto、Koji Morimoto、Ryosuke Ogawa、Toshifumi Dohi、Yasuyuki Kita

  DOI：10.1248/cpb.c16-00203

  日期：——

  Thioglycosides are available donors in glycosylation due to the stability of the anomeric C-S bond under general reaction conditions of protection and deprotection, and offer orthogonality in their activation. We report now that the hypervalent iodine effectively induced glycosylation reaction of thioglycosides with various alcohols. This method features a high efficiency, completion in a short time

  由于异头CS键在保护和脱保护的一般反应条件下的稳定性，硫糖苷是糖基化中可用的供体，并在它们的活化中提供正交性。现在我们报道，高价碘有效地诱导了硫糖苷与各种醇的糖基化反应。该方法效率高，可在短时间内完成并在非常温和的条件下进行。
• Catalytic Glycosylation with Glycosyl Thioimidate Donors
  作者：Cristina Lucas-Lopez、Niamh Murphy、Xiangming Zhu

  DOI：10.1002/ejoc.200800503

  日期：2008.9

  of glycosyl thioimidates, glycosyl N-phenyl-trifluorothioacetimidates, were prepared from the readily available glycosyl thiols in excellent yields. These imidates exhibited very good donor properties under the action of catalytic amounts of BF3·Et2O, and the corresponding glycosidation products were formed in very good to excellent yields. Thus, the first catalytic glycosylations with glycosyl thioimidate

  一类新的糖基硫代亚氨酸盐，即糖基 N-苯基-三氟硫代乙亚胺酸盐，是从容易获得的糖基硫醇以优异的产率制备的。这些亚胺酯在催化量的BF3·Et2O的作用下表现出非常好的供体性质，并且相应的糖苷化产物以非常好的收率形成。因此，实现了与糖基硫代亚氨酸酯供体的第一次催化糖基化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Enviromentally-Benign Glycosylation Reaction Using Odorless Thio-Glycosides and Hypervalent Iodine(III) Reagent
  作者：Yasuyuki Kita、Tetsuya Kajimoto、Koji Morimoto、Kana Yanase、Ibuki Odaka

  DOI：10.3987/com-18-s(f)35

  日期：——
• Helferich et al., Justus Liebigs Annalen der Chemie, 1926, vol. 447, p. 19,26
  作者：Helferich et al.

  DOI：——

  日期：——
• Helferich; Becker, Justus Liebigs Annalen der Chemie, 1924, vol. 440, p. 1,12
  作者：Helferich、Becker

  DOI：——

  日期：——