2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide | 573700-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide
• 英文别名: 2-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide；Bz(-2)[Bz(-3)][Bz(-4)]Rha(a1-2)a-Glc1Br3Ac4Ac6Ac；[(2S,3S,4R,5R,6S)-4,5-dibenzoyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-bromooxan-3-yl]oxy-2-methyloxan-3-yl] benzoate
• CAS: 573700-75-1
• 化学式: C₃₉H₃₉BrO₁₅
• 分子量: 827.634
• InChiKey: PTPSAQVCJVABDR-SDSVDUJPSA-N

物化性质

• 熔点：
  82-84 °C
• 沸点：
  821.3±65.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide 在 无水碳酸镉 、 camphor-10-sulfonic acid 、 胍 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.0h， 生成 diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides

  摘要：

  Two representative spirostanol saponins that have the typical structure for the sugar moiety, diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside (gracillin) and diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (dioscin), were easily synthesized by a general approach. A procedure using guanidine for the selective deblocking of acetyl while retaining benzoyl protecting groups is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00004-1
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose 在 4 A molecular sieve 、 三氟化硼乙醚 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides

  摘要：

  Two representative spirostanol saponins that have the typical structure for the sugar moiety, diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside (gracillin) and diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (dioscin), were easily synthesized by a general approach. A procedure using guanidine for the selective deblocking of acetyl while retaining benzoyl protecting groups is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00004-1

文献信息

• Total Synthesis and Structural Revision of Rebaudioside S, a Steviol Glycoside
  作者：Guo-En Wen、Hui Liu、Qi-Shuang Yin、Jin-Xi Liao、Yuan-Hong Tu、Qing-Ju Zhang、Jian-Song Sun

  DOI：10.1021/acs.joc.0c00442

  日期：2020.12.18

  considerable challenges in stereoselectivity control. Through systematic investigations, the effect of the internal glycosidic linkage configuration on the glycosylation stereoselectivity of 1,2-linked disaccharide donors was disclosed, and the intensified solvent effect by the 4,6-O-benzylidene protecting group was also observed with glucosyl donors. Through the orchestrated application of these favorable

  通过模块化策略研究了莱鲍迪甙S（一种来自甜叶菊的叶中的少量甜菊糖苷）的总合成，不仅完成了Reb-S及其类似物的第一个高效合成，而且还对最初的修订进行了总结建议的结构。模块化策略要求应用C2支链的二糖Yu供体来建立C-13甜菊醇糖苷键，这在立体选择性控制中提出了相当大的挑战。通过系统的研究，揭示了内部糖苷键构型对1,2-联二糖供体糖基化立体选择性的影响，以及4,6- O对溶剂的增强作用。在葡糖基供体中也观察到了亚苄基保护基。通过精心设计这些有益效果，可以很好地解决立体选择性问题。