butyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: butyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-butoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• 化学式: C₃₈H₄₄O₆
• 分子量: 596.764
• InChiKey: YZVBDOVFYQTXBZ-JTDOPDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-β-D-(4-monomethoxytrityl) thioglucoside 在 三乙胺 、 三氟乙酸 、 正丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 52.0h， 生成 butyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Exploring the Native Chemical Ligation Concept for Highly Stereospecific Glycosylation Reactions

  摘要：

  Various O-alkyl glycosides were obtained in a highly stereospecific manner with retention of configuration at the anomeric center. Our method has customized native chemical ligation concept for glycoconjugates synthesis, utilizing a meticulously controlled activating system. To explain the origin of stereoselective preference, an S(N)i mechanism was proposed and corroborated by computational calculations.

  DOI：

  10.1021/jo400020q

文献信息

• Stereoselective synthesis of glycosides using (salen)Co catalysts as promoters
  作者：Sandra Medina、Alexander S. Henderson、John F. Bower、M. Carmen Galan

  DOI：10.1039/c5cc02552d

  日期：——

  The use of (salen)Co catalysts as a new class of bench-stable stereoselective glycosylation promoters of trichloroacetimidate glycosyl donors at room temperature is described.

  (salen)Co催化剂在室温下作为一类新型的台式稳定的立体选择性糖基化促进剂，用于三氯乙酰亚胺糖基供体。
• Tris(pentafluorophenyl)borane-Promoted Stereoselective Glycosylation with Glycosyl Trichloroacetimidates under Mild Conditions
  作者：Kunj Bihari Mishra、Adesh Kumar Singh、Jeyakumar Kandasamy

  DOI：10.1021/acs.joc.8b00215

  日期：2018.4.6

  Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with trichloroacetimidate glycosyl donors is described. The reactions proceed efficiently with a wide range of acceptors, from sugar to nonsugar, under mild conditions in the presence of a catalytic amount of B(C6F5)3. The perbenzylated glucosyl α-imidate provides β-selective glycosides in 70–92% yields.

  描述了用三氯乙酰亚胺酸酯糖基供体的三（五氟苯基）硼烷促进的立体选择性糖基化。在催化量的B（C 6 F 5）3存在下，在温和条件下，反应可利用各种受体（从糖到非糖）有效地进行。过苄基化的葡萄糖基α-亚氨酸酯以70-92％的产率提供β-选择性糖苷。
• A 1,2-<i>trans</i> -Selective Glycosyl Donor Bearing Cyclic Protection at the C-2 and C-3 Hydroxy Groups
  作者：Nahoko Yagami、Hideki Tamai、Taro Udagawa、Akiharu Ueki、Miku Konishi、Akihiro Imamura、Hideharu Ishida、Makoto Kiso、Hiromune Ando

  DOI：10.1002/ejoc.201700671

  日期：2017.9.1

  A new 1,2-trans-selective glycosylation reaction is described. Glucosyl donors protected cyclically at the C-2 and C-3 hydroxy groups as six- (butane diacetal), seven- (tetraisopropyldisiloxanylidene), or eight- (2,3-o-xylylene) membered fused rings were synthesized in a straightforward manner. The glycosylation reactions of the glucosyl donors with various acceptors mainly generated β-glycosides under

  描述了一种新的 1,2-反式选择性糖基化反应。葡萄糖基供体在 C-2 和 C-3 羟基上被循环保护为六（丁烷二缩醛）、七（四异丙基二亚硅氧烷）或八（2,3-o-亚二甲苯基）元稠环，以直接方式合成. 在常规反应条件下，葡萄糖基供体与各种受体的糖基化反应主要生成β-糖苷。结果表明，从立体选择性和化学稳定性的角度来看，邻二甲苯基是合适的1,2-反式导向基团。通过核磁共振光谱和计算模拟对邻二甲苯保护的葡萄糖衍生物的氧代碳鎓离子进行了构象研究。结果表明氧碳鎓离子主要采用 4H3 构象，这是由于 C-2 和 C-3 处的刚性互稠环，而非环状保护的衍生物可能在构象之间波动。这些结果表明，C-2 处的伪赤道木氧基与传入的亲核试剂之间的相互作用阻碍了 1,2-顺式攻击。
• Stereoselective O-glycosylation reactions using glycosyl donors with diphenylphosphinate and propane-1,3-diyl phosphate leaving groups
  作者：Hariprasad Vankayalapati、Gurdial Singh、Isabelle Tranoy

  DOI：10.1016/s0957-4166(01)00227-0

  日期：2001.6

  Glycosyl donors having a diphenylphosphinate and a propane-1,3-diyl phosphate leaving group were easily prepared by the addition of the anomeric hydroxyl group of 2,3,4,6-tetra-O-benzyl-α,β-d-glucopyranose to diphenylphosphinic and propane-1,3-diyldioxyphosphoryl chlorides. These glycosyl donors were selectively glycosylated with a number of primary and secondary oxygen nucleophiles in the presence

  通过添加2,3,4,6-四-O-苄基-α，β-d-吡喃葡萄糖的异头羟基可以轻松制备具有二苯基次膦酸酯和丙烷1,3-二苯基磷酸酯离去基团的糖基供体生成二苯基次膦酸和丙烷1，，3-二基二氧基磷酰氯。在三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）存在下，这些糖基供体被许多伯和仲氧亲核试剂选择性糖基化。磷酸1，3-二烷基酯的使用导致β- O-连接的糖苷的立体选择性形成。
• Gold-catalysed glycosylation reaction using an easily accessible leaving group
  作者：Srinivasa Rao Koppolu、Ramana Niddana、Rengarajan Balamurugan

  DOI：10.1039/c5ob00248f

  日期：——

  Development of a simple leaving group for the gold-catalysed glycosylation has been achieved.

  已经实现了为金催化糖基化开发简单的脱离基团。