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2,3,4,6,2',3',4',6'-octa-O-benzyl-α,β-trehalose | 58781-27-4

中文名称
——
中文别名
——
英文名称
2,3,4,6,2',3',4',6'-octa-O-benzyl-α,β-trehalose
英文别名
(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxane
2,3,4,6,2',3',4',6'-octa-O-benzyl-α,β-trehalose化学式
CAS
58781-27-4
化学式
C68H70O11
mdl
——
分子量
1063.3
InChiKey
AVZQUDHQXONDDN-GFOBPCDQSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 密度:
    1.24±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    11
  • 重原子数:
    79
  • 可旋转键数:
    28
  • 环数:
    10.0
  • sp3杂化的碳原子比例:
    0.29
  • 拓扑面积:
    102
  • 氢给体数:
    0
  • 氢受体数:
    11

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Synthesis and Glycosylation Shift of 1,1'-Disaccharides.
    摘要:
    Nineteen kinds of nonreducing 1,1'-disaccharides have synthesized by modified Koenigs-Knorr method, and characterized by NMR. The glycosylation shift of each anomeric carbon has been estimated.
    DOI:
    10.1248/cpb.42.982
  • 作为产物:
    参考文献:
    名称:
    Isopropenyl glycosides and congeners as novel classes of glycosyl donors: theme and variations
    摘要:
    Isopropenyl glycosides (i.e., 10 and 11) have been synthesized in high yields by reacting the corresponding anomeric acetates with the Tebbe reagent. These compounds undergo glycosylation with primary or secondary carbohydrate alcohols in the presence of trimethylsilyl triflate or boron trifluoride etherate, probably via a mixed acetal glycoside intermediate. On the basis of this principle, a quite efficient glycosylation of monosaccharide hemiacetal donors (i.e., 1, 7, and 9) with acceptors bearing an isopropenyl ether function at a primary or secondary position (i.e., 18 and 21) has been developed. Also investigated were the glycosylating properties of isopropenyl glucosyl and galactosyl carbonates (i.e., 12-15), easily prepared from the corresponding hemiacetals, toward sugar alcohols. In each case, the beta-selective synthesis of disaccharides from donors having nonparticipating groups at C-2 was ensured by the use of acetonitrile, at low temperature, as the solvent.
    DOI:
    10.1021/ja00042a010
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文献信息

  • Molecular sieves promote stereocontrolled αα-disaccharide formation via direct dimerization of free sugars
    作者:Gary H. Posner、D.Scott Bull
    DOI:10.1016/0040-4039(96)01376-7
    日期:1996.8
    Some commercial molecular sieves promote direct dimerization of free pyranose and furanose sugars stereoselectively into the corresponding α,α-disaccharides.
    一些商业分子筛促进游离的喃糖和呋喃糖糖立体选择性地直接二聚为相应的α,α-二糖。
  • Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2‐Aryl‐1,3‐dithiane 1‐Oxide <sup>†</sup>
    作者:Lei Cai、Jing Zeng、Ting Li、Ying Xiao、Xiang Ma、Xiong Xiao、Qin Zhang、Lingkui Meng、Qian Wan
    DOI:10.1002/cjoc.201900419
    日期:2020.1
    center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3‐diol protection. Most
    利用三氟甲磺酸酐(Tf 2O)。通过将高亲性启动子系统的高效性与脱糖基化的逐步效率相结合,该试剂通过C1-半乙缩醛供体进行了分子间的氧代缩醛化反应,以安装一个临时的离去基团,从而使远程位置的瞬变亲电子中心变为异头位置。拴在末端的三氟甲磺酸亚砜在分子内同时活化了硫化物,提供了碳碳鎓离子,从而促进了标题糖基化。除了可容纳广泛的官能团和不活跃的半缩醛底物外,目前的激活方案还证明了对1,3-二醇的保护是合宜的。最重要的是,该方法进一步为将化学应用于碳水化合物化学提供了新的视角。
  • A New, Efficient Glycosylation Method for Oligosaccharide Synthesis under Neutral Conditions:  Preparation and Use of New DISAL Donors
    作者:Lars Petersen、Knud J. Jensen
    DOI:10.1021/jo0057654
    日期:2001.9.1
    Efficient, stereoselective glycosylation methods are required for the synthesis of complex oligosaccharides as tools in glycobiology. All glycosylation methods, which have found wide acceptance, rely on Lewis acid activation of glycosyl donors prior to glycosylation. Here, we present a new and efficient method for glycosylation under neutral or mildly basic conditions. Glycosides of methyl 2-hydroxy-3
    需要高效,立体选择性的糖基化方法来合成复杂的寡糖,并将其作为糖生物学的工具。已经被广泛接受的所有糖基化方法都依赖于糖基化之前糖基供体的路易斯酸活化。在这里,我们提出了一种在中性或轻度碱性条件下糖基化的新方法。通过亲核芳族取代制备2-羟基-3,5-二硝基苯甲酸甲酯(DISAL)及其对位异构体4-羟基-3,5-二硝基苯甲酸甲酯的糖苷。在它们作为糖基供体的潜力的第一个证明中,实现了甲醇的立体定向糖基化。在受阻醇的糖基化反应中,β-给体被证明具有更高的反应性,并且主要形成了α-葡萄糖苷。被保护的单糖的糖基化,在没有路易斯酸和碱的情况下,在40-60℃下于1-甲基-2-吡咯烷酮NMP)中平稳地进行与游离的6-OH或3-OH的反应,获得了良好的产率。3-OH的糖基化仅产生α-连接的二糖。
  • Reactions on phenyl chlorosulfate at OH-1, -4, and -6 of aldohexopyranose derivatives. Formation of 1,2-oxazoline and 4,6-cyclic sulfate rings
    作者:Magdy M. Abdel-Malik、Arthur S. Perlin
    DOI:10.1016/0008-6215(89)84091-1
    日期:1989.6
    little or no interference with disaccharide synthesis at the nearby O-4 atom. Conformations of both cis - and trans -fused types of 4,6-cyclic sulfates are discussed. At an unsubstituted anomeric center, the course of reaction by phenyl chlorosulfate is determined by neighboring-group participation possibilities, and the strong leaving-group affinity of a phenylsulfate substituent. This is demonstrated
    摘要在苯基硫酸氢钠与不含OH-4和OH-6的化合物的反应中,例如在甲基2,3-二-O-苄基醛基喃糖苷中,伯羟基发生区域选择性取代,或者4,取决于实验条件,形成6-环硫酸盐。向二-O-苄基糖苷中添加6-(苯硫酸盐)取代基似乎几乎不干扰或几乎不干扰附近的O-4原子处的二糖合成。讨论了4,6-环硫酸盐的顺式和反式融合形式的构象。在未取代的异头异构中心,硫酸苯酯的反应过程取决于相邻基团的参与可能性以及苯硫酸酯取代基的强离去基团亲和力。2-乙酰基-4的60%转化证明了这一点,
  • Nouvelle méthode de synthèse Stéréosélective de glycosides. Syntèse des α,α-tréhalose, analogues galacto, manno et autres α-d-glycosides
    作者:André A. Pavia、Jean-Michel Rocheville、Sak N. Ung
    DOI:10.1016/s0008-6215(00)85133-2
    日期:1980.2
    corresponding α,α-(1 → 1) and α,β-(1 → 1) disaccharides. Hence, pure 2,3,4,6,2′,3′,4′,6 - octa-O-benzyl derivatives of α,α-trehalose, and the d -galacto and d -manno analogues were obtained, after column chromatography, in 55–65% yield. Hydrogenolysis gave the corresponding free sugars. The pure anomers were obtained in 10–34% yield. The potentiality of the method was demonstrated by the synthesis of 2,3
    摘要在三氟甲磺酸三氟甲磺酸)酐为催化剂,二氯甲烷为溶剂的情况下,在低温下存在2,3,4,6-四-O-苄基-d-葡萄糖,2,3,4,6-四-O -苄基-d-喃半乳糖和2,3,4,6-四-O-苄基-d-甘露喃糖几乎定量地转化为相应的α,α-(1→1)和2:1混合物α,β-(1→1)二糖。因此,在柱后,获得了α,α-海藻糖的纯2,3,4,6,2',3',4',6-辛基-O-苄基衍生物,以及d-半乳糖和d-甘露糖类似物。层析,产率55-65%。氢解得到相应的游离糖。以10–34%的产率获得纯的异头物。该方法的潜力通过合成2,3,4,6-四-O-苄基-α-d-葡萄糖基2,3:4,5-二-O-异亚丙基-β-d-果糖喃糖苷来证明。 50%的产量,
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