2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-D-glucopyranoside | 544686-94-4

• 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-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-D-glucopyranoside
• 英文别名: 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,3,4-tetra-O-benzoyl-D-glucopyranose；1,2,3,4-tetra-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-α/β-D-glucopyranose；Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Glc-O-Bz；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R)-3,4,5,6-tetrabenzoyloxyoxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 544686-94-4
• 化学式: C₆₈H₅₄O₁₉
• 分子量: 1175.17
• InChiKey: KKEIVOQTXWVXGA-GNLLKUEPSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  87
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-D-glucopyranoside 在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  从 Oroxylum indium 的种子中分离出的天然黄酮苷、oroxins C 和 D 的简明合成和抗糖尿病活性

  摘要：

  从 Oroxylum indicum 的种子中分离出的天然黄酮苷类化合物 C (1) 和 D (2) 的首次简洁合成是通过收敛策略有效实现的。这 ...

  DOI：

  10.1177/1747519820927966
• 作为产物：
  描述：

  gentibiose 、 苯甲酰氯 在 吡啶 作用下， 以98%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-D-glucopyranoside
  参考文献：
  名称：

  A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues

  摘要：

  Based on 1,2-O-isopropylidene-sn-glycerol five chiral building blocks containing differently modified glycerol residues were required for the synthesis of the target molecule 2. One of these building blocks is diacylglyceryl beta-gentiobioside carrying a phosphite residue at 6b-O position. Ligation of these five building blocks led to the desired glycerol phosphate backbone to which D-alanyl residues were attached, thus generating after O-deprotection the target molecule 2, a bisamphiphilic structural variant of Staphylococcus aureus LTA. This compound displayed higher potency in terms of cytokine release by human blood leukocytes than the monoamphiphilic variant LTA. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.055

文献信息

• STICS: surface-tethered iterative carbohydrate synthesis
  作者：Papapida Pornsuriyasak、Sneha C. Ranade、Aixiao Li、M. Cristina Parlato、Charles R. Sims、Olga V. Shulga、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1039/b817684a

  日期：——

  A new surface-tethered iterative carbohydrate synthesis (STICS) technology is presented in which a surface functionalized ‘stick’ made of chemically stable high surface area porous gold allows one to perform cost efficient and simple synthesis of oligosaccharide chains; at the end of the synthesis, the oligosaccharide can be cleaved off and the stick reused for subsequent syntheses.

  提出了一种新的表面固定的迭代碳水化合物合成（STICS）技术，该技术使用了由化学稳定的高表面积多孔金制成的表面功能化“棒”，能够高效且简单地合成寡糖链；在合成结束时，可以将寡糖从棒上切下，并可将棒重复用于后续合成。
• Synthesis of 12-<i>O</i>-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle
  作者：Le Van Huy、Chiaki Tanaka、Takashi Imai、Sho Yamasaki、Tomofumi Miyamoto

  DOI：10.1021/acsmedchemlett.8b00413

  日期：2019.1.10

  Fifteen glycosyl-oxystearates were synthesized by Crich's 4,6-benzylidene and Koening-Knorr strategies. Assessment of structure-activity relationships using macrophage-inducible C-type lectin (Mincle) receptor cells expressing nuclear factor of activated T cells (NFAT)-green fluorescent protein (GFP) revealed that four dimannopyranosyl-oxystearate analogues were Mincle agonists and that 12-O-(2-O-alpha-D-mannopyranosyl)-alpha-D-mannopyranosyl-oxystearate was as an activator of both mouse and human Mincle.
• Total Synthesis of the Antiallergic Naphtho-α-pyrone Tetraglucoside, Cassiaside C₂, Isolated from Cassia Seeds
  作者：Zhaojun Zhang、Biao Yu

  DOI：10.1021/jo034223u

  日期：2003.8.1

  Toralactone 9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1, cassiaside C-2) isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-alpha-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.
• Facile synthesis of three bidesmosidic oleanolic acid saponins with strong inhibitory activity on pancreatic lipase
  作者：Tiantian Guo、Qingchao Liu、Peng Wang、Lei Zhang、Wei Zhang、Yingxia Li

  DOI：10.1016/j.carres.2009.04.024

  日期：2009.7

  The first synthesis of scabiosaponins E (1), F (2), and G (3), three new oleanolic acid saponins with strong inhibitory activity on pancreatic lipase isolated from the Chinese traditional medicinal herb Scabiosa tschiliensis, was efficiently achieved in an one-pot strategy under the combined use of glycosyl trichloro-acetimidates and p-toluene 1-thioglycosides (STol) as donors. (C) 2009 Published by Elsevier Ltd.