1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside | 103931-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: 1',2,3,3',4,4',6'-hepta-O-benzylsucrose；[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-2,5-bis(phenylmethoxymethyl)oxolan-2-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 103931-59-5
• 化学式: C₆₁H₆₄O₁₁
• 分子量: 973.173
• InChiKey: XJSQRSYAUQRCJO-FZPLEZICSA-N

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：

  1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 磷酸 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 二甲基亚砜 为溶剂， 生成 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-carbaldehyde
  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
• 作为产物：
  描述：

  1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl-2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside 在 三氟乙酸 作用下， 以 氯仿 、 水 为溶剂， 以75%的产率得到1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4-tri-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

• Self-Assembling Properties of 6-<i>O</i>- and 6′-<i>O</i>-Alkylsucrose Mixtures Having Different Chain Lengths Under Aqueous Conditions
  作者：Kouhei Tanaka、Sachie Ohkawabata、Kazuya Yamamoto、Jun-ichi Kadokawa

  DOI：10.1080/07328303.2013.809094

  日期：2013.5.4

  The self-assembling properties of the 6-O- and 6-O-alkylsucrose mixtures with different chain lengths including octyl, decyl, dodecyl, and tetradecyl under aqueous conditions were studied and compared with those of the 6-O- and 6-O-hexadecylsucrose mixture previously reported. The title compounds were synthesized from sucrose in five steps. The results of scanning and transmission electron microscopes, powder X-ray diffraction, and dynamic light scattering measurements indicated that the self-assembling properties of octyl, decyl, and dodecyl derivatives were completely different from those of the 6-O- and 6-O-hexadecylsucrose mixture. The three derivatives reported here primarily formed lamellar planes, which further induced the formation of vesicle-type particles under aqueous conditions, whereas the previous derivatives primarily formed spherical micelles in water, which further assembled according to face-centered cubic organization by a drying process from the aqueous dispersion. It was also found that the 6-O- and 6-O-tetradecylsucrose mixture showed concentration-induced micelle-lamellar transition behavior in an aqueous dispersion. Furthermore, the mixing of a regioisomer, 6-O-hexadecylsucrose, with 6-O-hexadecylsucrose induced different self-assembling properties from that of 6-O-hexadecylsucrose alone, but this effect did not appear in the self-assembling of the 6-O- and 6-O-octylsucrose mixture.
• Self-assembly of 6-O- and 6′-O-hexadecylsucroses mixture under aqueous conditions
  作者：Manami Kanemaru、Shin-ya Kuwahara、Kazuya Yamamoto、Yoshiro Kaneko、Jun-ichi Kadokawa

  DOI：10.1016/j.carres.2010.10.003

  日期：2010.12

  In this paper we report the self-assembly of 6-O- and 6'-O-hexadecylsucroses mixture under aqueous conditions The mixture was synthesized by a five-step sequence from sucrose The SEM image of a sample prepared by drying a dispersion of the mixture in water showed nanoparticles with the diameter of similar to 50 nm and aggregates that were formed by further assembly of them The XRD measurement of the sample exhibited the diffraction pattern assignable to face-centered cubic (FCC) structure and the diameter of a sphere which took part in the FCC structure was calculated to be 5 1 nm This value was relatively close to that observed in the DLS measurement of a dispersion of the mixture in water and estimated for a spherical micelle based on the molecular sizes of the two sucrose ethers On the basis of the above findings the following self-assembly process of the mixture under aqueous conditions was proposed The mixture formed the spherical micelles with the diameter of similar to 5-7 nm in water The micelles regularly organized according to the FCC structure during the drying process from the aqueous dispersion to construct the nanoparticles with the diameter of similar to 50 nm Several numbers of the nanoparticles further assembled to form the aggregates (C) 2010 Elsevier Ltd All rights reserved