6-O-（三苯甲基）-D-吡喃葡萄糖四乙酸酯 | 67919-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 6-O-（三苯甲基）-D-吡喃葡萄糖四乙酸酯
• 英文名称: 1,2,3,4-tetra-O-acetyl-6-O-trityl-D-glucopyranoside
• 英文别名: 1,2,3,4-tetra-O-acetyl-6-O-trityl-D-glucopyranose；1,2,3,4-tetra-O-acetyl-6-O-trityl-glucopyranose；6-trityl-1,2,3,4-tetra-O-acetyl-D-glucose；6′-O-trityl-1′,2′,3′,4′-tetra-O-acetyl-D-glucose；[(2R,3R,4S,5R)-4,5,6-triacetyloxy-2-(trityloxymethyl)oxan-3-yl] acetate
• CAS: 67919-36-2
• 化学式: C₃₃H₃₄O₁₀
• 分子量: 590.627
• InChiKey: GTJGUFOLNHYRQE-MDKHBBSCSA-N

物化性质

• 沸点：
  633.3±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 溶解度：
  二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-O-（三苯甲基）-D-吡喃葡萄糖四乙酸酯 在 氢溴酸 、 溶剂黄146 、 苄胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 54.52h， 生成 gentiobiose hepta-acetate
  参考文献：
  名称：

  Synthesis of leptosin, a glycoside isolated from mānuka honey

  摘要：

  The first synthesis of leptosin, a novel glycoside isolated from manuka honey is described. Utilising an acetyl protecting group strategy the glycoside was obtained with excellent anomeric selectivity by deploying a Schmidt glycosylation as a key step. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.042
• 作为产物：
  描述：

  三苯基氯甲烷 在 吡啶 、 三乙胺 作用下， 反应 6.0h， 生成 6-O-（三苯甲基）-D-吡喃葡萄糖四乙酸酯
  参考文献：
  名称：

  BODIPY-Based Analogue of the TREM2-Binding Molecular Adjuvant Sulfavant A, a Chemical Tool for Imaging and Tracking Biological Systems

  摘要：

  DOI：

  10.1021/acs.analchem.3c04322

文献信息

• Total synthesis of agalloside, isolated from Aquilaria agallocha, by the 5-O-glycosylation of flavan
  作者：Midori A. Arai、Yumi Yamaguchi、Masami Ishibashi

  DOI：10.1039/c7ob01004d

  日期：——

  Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic

  Agalloside（1）是我们小组使用固定化Hes1的珠子从沉香中分离得到的神经干细胞分化激活剂。我们进行agalloside（第一全合成1）经由5- ø的黄烷-glycosylation 25使用糖基氟化物20在BF的存在3 ·的Et 2 O.用DDQ随后的氧化，以黄烷酮2和脱保护依次agalloside提供（1）。该合成策略有望用于合成5- O-糖基化的类黄酮。合成的galloloside（1）加速了神经干细胞的分化，其结果可与天然化合物1媲美。
• Inhibition of <i>S. aureus</i> Infection of Human Umbilical Vein Endothelial Cells (HUVECs) by Trehalose‐ and Glucose‐Functionalized Gold Nanoparticles
  作者：Yimeng Li、Nicholas Ariotti、Behnaz Aghaei、Elvis Pandzic、Sylvia Ganda、Mark Willcox、Manuel Sanchez‐Felix、Martina Stenzel

  DOI：10.1002/anie.202106544

  日期：2021.10.11

  ability to prevent binding to endothelial cells. Acting as anti-adhesive agents, trehalose-functionalized NPs decreased the binding of S. aureus to HUVECs, while outperforming the control NPs. Microscopy revealed that trehalose-coated NPs bound strongly to S. aureus compared to the controls. In conclusion, nanoparticles based on trehalose could be a non-toxic alternative to inhibit S. aureus infection

  微生物对宿主细胞的粘附是感染过程的第一步。已经探索了几种抑制微生物粘附的方法，包括使用基于甘露糖、半乳糖、唾液酸和葡萄糖的糖聚合物。然而，这些糖受体在体内大量存在，并非细菌所独有。相比之下，海藻糖是一种独特的二糖，被微生物广泛表达。这种碳水化合物还没有被用作抗粘剂。在此，制备了涂有海藻糖基聚合物的金纳米粒子 (AuNPs)，并与葡萄糖功能化的 AuNPs 进行了比较，并检查了它们防止与内皮细胞结合的能力。作为抗粘剂，海藻糖功能化的 NPs 降低了金黄色葡萄球菌的结合到 HUVEC，同时优于对照 NP。显微镜显示，与对照相比，海藻糖包被的 NPs 与金黄色葡萄球菌结合牢固。总之，基于海藻糖的纳米颗粒可能是抑制金黄色葡萄球菌感染的无毒替代品。
• Solution and solid-phase chemoselective synthesis of (1-6)-amino(methoxy) di- and trisaccharide analogues
  作者：Francesco Peri、Alexander Deutman、Barbara La Ferla、Francesco Nicotra

  DOI：10.1039/b203605c

  日期：2002.7.1

  Disaccharide and trisaccharide mimics containing the amino(methoxy) interglycosidic linkage were obtained by chemoselective condensation of unprotected aldoses in an aqueous environment both in solution and in solid phase.

  含有氨基（甲氧基）糖苷间键的二糖和三糖模拟物是通过未保护的醛糖在水性溶液中和固相中的化学选择性缩合而获得的。
• Synthesis of cytidine diphosphate-d-quinovose
  作者：Li-da Liu、Hung-wen Liu

  DOI：10.1016/s0040-4039(01)80315-4

  日期：——
• 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.