1,3,4-tri-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 103931-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4-tri-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: 1',2,3,3',4,4',6-hepta-O-benzyl-sucrose；1',2,3,3',4,4',6-hepta-O-benzylsucrose
• CAS: 103931-54-0
• 化学式: C₆₁H₆₄O₁₁
• 分子量: 973.173
• InChiKey: RSFNICIIZNMESD-FZPLEZICSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.18
• 重原子数：
  72.0
• 可旋转键数：
  26.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  112.53
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1,3,4-tri-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 sodium azide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成 1′,2,3,3′,4,4′,6-hepta-O-benzyl-6′-amino-6′-deoxysucrose
  参考文献：
  名称：

  Amide-linked N-methacryloyl sucrose containing polymers

  摘要：

  1',2,3,3',4,4',6-Hepta-O-benzyl-6'-N-methacryloyl-6'-deoxysucrose 1, 6'-deoxy-6'-N-methacryloyloxyethylureido sucrose 2 and 6,6'-dideoxy-6,6'-N-dimethacryloyloxyethylureido sucrose 3 have been homo-polymerized and copolymerized with styrene by a free radical process, yielding polymer materials with pendant sucrose moieties, attached to the polymer backbone via amide linkages. The results demonstrated that varying the structural features of the monomers, greatly affected the thermal and rheological properties of the polymers. The polymer materials obtained have been characterized by NMR, MALDI-TOF, DSC, AFM and EWC (equilibrium water content). The efficient synthesis of the three novel, regioisomerically pure, N-methacryloylamide sucrose-containing monomers (1, 2 and 3) have been described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2014.03.050
• 作为产物：
  描述：

  1,3,4-tri-O-benzyl-6-O-trityl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 三氟乙酸 作用下， 以 氯仿 、 水 为溶剂， 反应 0.33h， 以78%的产率得到1,3,4-tri-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  蔗糖的C-甲基化：6-和6'-C-甲基蔗糖的合成

  摘要：

  摘要通过酸催化水解6'-O-三苯甲基衍生物得到的2,3,4,6,1'，3'，4'-Hepta-O-苄基蔗糖用Pfitzner-Moffatt试剂和将产物用甲基碘化镁烷基化。然后除去保护基团，得到非对映异构体的混合物，即7-脱氧-β-d-α-硝基和-α-1--1-半乳糖-庚-2-铀酰呋喃糖基α-d-吡喃葡萄糖苷。将该反应序列应用于2,3,4,1'，3'，4'，6'-庚基-O-苄基蔗糖，得到β-d-果糖呋喃糖基7-脱氧-dl-甘油-α-d-葡萄糖-七吡喃糖苷。

  DOI：

  10.1016/s0008-6215(00)90395-1

文献信息

• Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system
  作者：Yue-tao Zhao、Shan Niu、Lu-bai Huang、Ji-ming Wang、Zhao-jun Yin、Qing Li、Zhong-jun Li

  DOI：10.1016/j.tet.2013.03.094

  日期：2013.6

  key step is the regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system, followed by a high α-selective glycosylation. The newly developed de-O-benzylation system is efficient in removing the primary benzyl groups of sucrose and raffinose under mild condition and with high selectivity. Using thioglycoside as donor, NIS/AgOTf as promoter and DTBMP as additive, glycosylation of acid labile sucrose

  提出了一种方便的方法，以蔗糖为原料合成棉子糖，水苏糖和马齿c糖。关键步骤是使用Co 2（CO）8 / Et 3 SiH / CO系统进行区域选择性脱O-苄基化，然后进行高水平的α-选择性糖基化。新开发的脱-O-苄基化系统可在温和条件下以高选择性高效去除蔗糖和棉子糖的伯苄基。使用硫代糖苷作为供体，NIS / AgOTf作为启动子，DTBMP作为添加剂，酸不稳定蔗糖底物的糖基化可以实现高收率。
• Hydrogen-Bond-Mediated Aglycone Delivery: Synthesis of β-<scp>d</scp>-Fructofuranosides
  作者：Pan Wang、Yidian Mo、Xiaoyu Cui、Xuyang Ding、Xiao Zhang、Zhongjun Li

  DOI：10.1021/acs.orglett.0c00702

  日期：2020.4.17

  work, we developed an efficient method for the synthesis of β-d-fructofuranosides by using a 6-picoloyl-protected fructofuranosyl thioglycoside as the glycosyl donor. Subsequently, we applied the approach to a wide variety of donors and acceptors. Furthermore, the successful synthesis of levantetrose confirmed its applicability in the multistep synthesis of oligosaccharides.

  β- d-果糖呋喃糖苷键的构建是碳水化合物化学中的主要挑战之一。在这项工作中，我们开发了用于β-的合成的有效方法d通过使用6 picoloyl保护的果糖基硫代糖苷作为糖基供体-fructofuranosides。随后，我们将该方法应用于各种捐赠者和接受者。此外，Levantetrose的成功合成证实了其在寡糖的多步合成中的适用性。
• Bromine in Methanol: An Efficient Reagent for the Deprotection of the tert-Butyldiphenylsilyl Group
  作者：M. Teresa Barros、Christopher D. Maycock、Christine Thomassigny

  DOI：10.1055/s-2001-15136

  日期：——

  A selective reagent for the deprotection of a tert-butyl-diphenylsilyl (TBDPS) ether in the presence of other protecting groups, using a solution of bromine in methanol under reflux is presented. By extension, this reagent has been introduced for the deprotection of TBDPS amines and esters and has also shown good selectivity in the removal of a TBDMS ether in the presence of a TBDPS one.

  介绍了一种选择性试剂，该试剂在回流条件下使用溴在甲醇中的溶液，对存在其他保护基团的叔丁基二苯基硅烷（TBDPS）醚进行脱保护。此外，该试剂还可用于 TBDPS 胺和酯的脱保护，并在去除存在 TBDPS 的 TBDMS 醚时显示出良好的选择性。
• Potentially Biodegradable Polymers Based on α- or β-Pinene and Sugar Derivatives or Styrene, Obtained under Normal Conditions and on Microwave Irradiation
  作者：Maria Teresa Barros、Krasimira T. Petrova、Ana Maria Ramos

  DOI：10.1002/ejoc.200600890

  日期：2007.3

  The homopolymerisation of α- and β-pinene and their copolymerisation with styrene and hepta-O-benzyl-6′-O-methacryloyl-sucrose (BMS) have been examined in the presence of AIBN as free-radical initiator, either in toluene or without solvent at 80 °C at normal pressure and also in a synthetic microwave oven. A study of the effect of the reaction conditions, the monomer structure and the initial ratio

  α-和β-蒎烯的均聚以及它们与苯乙烯和七-O-苄基-6'-O-甲基丙烯酰基-蔗糖（BMS）的共聚已经在AIBN作为自由基引发剂的存在下，在甲苯或在 80 °C 和常压下以及合成微波炉中无溶剂。已经对反应条件、单体结构和共聚单体的初始比例对最终共聚物性质的影响进行了研究，每一种都含有两种天然产物。发现了一种在微波辐射温和条件下在短反应时间内合成聚（β-蒎烯）、聚（α-蒎烯-共聚苯乙烯）和聚（β-蒎烯-共聚苯乙烯）的新方法。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Novel Unsaturated Sucrose Ethers and Their Application as Monomers
  作者：Carina Crucho、Krasimira Petrova、Rui Pinto、Maria Barros

  DOI：10.3390/molecules13040762

  日期：——

  Novel unsaturated ethers were synthesised in good yields starting from sucrose,using a two-step mild and efficient procedure based on the Gassman method, which consists in forming a vinyl group by the elimination of ethanol from mixed acetals with trimethylsilyl trifluoromethanesulfonate in the presence of alkyl amines. Mixed acetals are readily obtained from the corresponding alcohols and ethyl vinyl

  以蔗糖为原料，采用温和高效的两步法合成了新型不饱和醚，该方法基于 Gassman 方法，该方法包括在烷基存在下通过三甲基甲硅烷基三氟甲磺酸酯从混合缩醛中消除乙醇形成乙烯基。胺类。使用酸性催化剂，很容易从相应的醇和乙基乙烯基醚中获得混合缩醛。还研究了涉及初级卤化物的常规醚化。如此获得的单体通过自由基机制成功聚合，产生具有未决蔗糖部分的无支链线性和可溶性聚合物，并测定了它们的一些物理性质。