3-β-D-galactopyranosyl-1-propene | 129706-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-β-D-galactopyranosyl-1-propene
• 英文别名: (2R,3R,4R,5R,6S)-2-(hydroxymethyl)-6-prop-2-enyloxane-3,4,5-triol
• CAS: 129706-77-0
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: JDPNGXUXFIFPNG-QKAWAISNSA-N

物化性质

• 熔点：
  120-122 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  382.7±42.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-β-D-galactopyranosyl-1-propene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以66%的产率得到1-β-D-galactopyranosylpropane
  参考文献：
  名称：

  N-Substituted (β-d-galactopyranosylmethyl)amines, and C-β-d-galactopyranosylformamides, and related compounds

  摘要：

  DOI：

  10.1016/0008-6215(90)84186-x
• 作为产物：
  描述：

  1-deoxy-1-allyl-2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-galactopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-β-D-galactopyranosyl-1-propene
  参考文献：
  名称：

  Hydration IndexA Better Parameter for Explaining Small Molecule Hydration in Inhibition of Ice Recrystallization

  摘要：

  Several simple mono- and disaccharides have been assessed for their ability to inhibit ice recrystallization. Two carbohydrates were found to be effective recrystallization inhibitors. D-Galactose (1) was the best monosaccharide and D-melibiose (5) was the most active disaccharide. The ability of each carbohydrate to inhibit ice growth was correlated to its respective hydration number reported in the literature. A hydration number reflects the number of tightly bound water molecules to the carbohydrate and is a function of carbohydrate stereochemistry. It was discovered that using the absolute hydration number of a carbohydrate does not allow one to accurately predict its ability to inhibit ice recrystallization. Consequently, we have defined a hydration index in which the hydration number is divided by the molar volume of the carbohydrate. This new parameter not only takes into account the number of water molecules tightly bound to a carbohydrate but also the size or volume of a particular solute and ultimately the concentration of hydrated water molecules. The hydration index of both mono- and disaccharides correlates well with experimentally measured RI activity. C-Linked derivatives of the monosaccharides appear to have RI activity comparable to that of their O-linked saccharides but a more thorough investigation is required. The relationship between carbohydrate concentration and RI activity was shown to be noncolligative and a 0.022 M solution of D-galactose (1) and C-linked galactose derivative (10) inhibited recrystallization as well as a 3% DMSO solution. The carbohydrates examined in this study did not possess any thermal hysteresis activity (selective depression of freezing point relative to melting point) or dynamic ice shaping. As such, we propose that they are inhibiting recrystallization at the interface between bulk water and the quasi liquid layer (a semiordered interface between ice and bulk water) by disrupting the preordering of water.

  DOI：

  10.1021/ja806284x

文献信息

• Synthesis of <i>C</i> ‐Glycosyl Amino Acid Building Blocks Suitable for the Solid‐Phase Synthesis of Multivalent Glycopeptide Mimics
  作者：Niels R. M. Reintjens、Tony S. Koemans、Nick Zilverschoon、Riccardo Castelli、Robert A. Cordfunke、Jan Wouter Drijfhout、Nico J. Meeuwenoord、Herman S. Overkleeft、Dmitri V. Filippov、Gijsbert A. Marel、Jeroen D. C. Codée

  DOI：10.1002/ejoc.202000587

  日期：2020.8.31

  C-glycosyl functionalized lysine building blocks, featuring C-glycosidic derivatives of alpha-rhamnose, alpha-mannose, alpha-galactose, beta-galactose, and beta-N-acetyl glucosamine have been designed and synthesized. These derivatives, equipped with acid-labile protecting groups, are eminently suitable for solid-phase synthesis of multivalent glycopeptides. The lysine building blocks were prepared fromC-allyl

  已经设计并合成了五个 C-糖基功能化赖氨酸构件，其特征是 α-鼠李糖、α-甘露糖、α-半乳糖、β-半乳糖和β-N-乙酰氨基葡萄糖的 C-糖苷衍生物。这些衍生物带有酸不稳定保护基团，非常适合多价糖肽的固相合成。赖氨酸结构单元由 C-烯丙基糖苷制备，该糖苷经历了与丙烯酸酯的 Grubbs 交叉复分解，然后还原所得 α,β-不饱和酯中的 C=C 双键，并释放羧酸酯以允许缩合带有赖氨酸侧链。将由此得到的C-糖苷共五种，用于三种糖肽的固相肽合成(SPPS)，
• Switching between <i>X</i>-Pyrano-, <i>X</i>-Furano-, and Anhydro-<i>X</i>-pyranoside Synthesis (X = C, N) under Lewis acid Catalyzed Conditions
  作者：Youngran Seo、Jared M. Lowe、Neyen Romano、Michel R. Gagné

  DOI：10.1021/acs.orglett.1c01713

  日期：2021.8.6

  A variety of C-glycosides can be obtained from the fluoroarylborane (B(C6F5)3) or silylium (R3Si+) catalyzed functionalization of 1-MeO- and per-TMS-sugars with TMS-X reagents. A one-step functionalization with a change as simple as the addition order and/or Lewis acid and TMS-X enables one to afford chiral synthons that are common (C-pyranosides), have few viable synthetic methods (C-furanosides)

  各种C-糖苷可以从氟芳基硼烷(B(C 6 F 5 ) 3 )或硅基(R 3 Si + )催化的1-MeO-和全TMS-糖与TMS-X试剂的官能化获得。一步功能化只需简单地改变加成顺序和/或路易斯酸和 TMS-X，即可获得常见的手性合成子（ C-吡喃糖苷），但几乎没有可行的合成方法（ C-呋喃糖苷），或实际上是未知的（脱水-C-吡喃糖苷），其机械地分别由是否发生直接取代、异构化/取代或取代/异构化而产生。
• OLEFIN METATHESIS REACTIONS OF AMINO ACIDS, PEPTIDES AND PROTEINS CONTAINING ALLYL SULFIDE GROUPS
  申请人：Lin Yuya Angel

  公开号：US20120178913A1

  公开（公告）日：2012-07-12

  A method for the modification of an amino acid, protein or peptide is disclosed. The method comprises reacting a carbon-carbon double bond-containing compound with an amino acid, a protein or a peptide containing an allyl sulfide group in the presence of a catalyst which promotes olefin metathesis, to form a modified amino acid, protein or peptide. Preferred carbon-carbon double bond-containing compounds include carbohydrates.

  揭示了一种用于修饰氨基酸、蛋白质或肽的方法。该方法包括在促进烯烃交换反应的催化剂存在下，将含有碳-碳双键的化合物与含有烯丙基硫醚基团的氨基酸、蛋白质或肽反应，以形成修饰后的氨基酸、蛋白质或肽。首选的碳-碳双键含有化合物包括碳水化合物。
• Design and synthesis of C-linked fucosides as inhibitors of E-selectin
  作者：Taketo Uchiyama、Thomas J. Woltering、Weichyun Wong、Chun-Cheng Lin、Tetsuya Kajimoto、Maki Takebayashi、Gabriel Wéitz-Schmidt、Tetsuo Asakura、Masatoshi Noda、Chi-Huey Wong

  DOI：10.1016/0968-0896(96)00127-7

  日期：1996.7

  Two series of C-linked fucosides as mimetics for the tetrasaccharide sialyl Lewis X have been synthesized and tested as inhibitors of E-Selectin. The fucopeptides have been prepared from three key intermediates, including alpha-C-allyl fucose, natural and unnatural amino acids bearing hydroxyl groups and an alpha,omega-diacid moiety for the imitation of the essential three parts of SLe(x), i.e., the Fuc, Gal, and NeuAc. The nature and distance of the linkage of the fucose moiety to the amino acids as well as the distance between the amino acids and the terminal carboxylic acid group turned out to be crucial for the biological activity. In addition the necessity of both OH groups (4- and 6-OH) in the Gal part could be confirmed. Conformational NMR study of the most active mimetic supports the structure-activity relationship. A second series of mimetics was prepared, where Fuc and Gal moieties were purely C-linked. In the synthesis of beta-C-allyl galactose an intramolecular 1,2-hydride shift led to an interesting side product. However, the substituted glycosidic oxygens led to a substantial loss of conformational constrain, which could not be compensated and resulted in low activity. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of α-Gal epitope derivatives with a galactosyltransferase–epimerase fusion enzyme
  作者：Jianwen Fang、Xi Chen、Wei Zhang、Adam Janczuk、Peng George Wang

  DOI：10.1016/s0008-6215(00)00245-7

  日期：2000.12

  beta -Gal epitopes are carbohydrate structures bearing an alpha -D-Galp-(1 --> 3)-beta -D-Galp terminus and are the main cause of antibody-mediated hyperacute rejection in xenotransplantation. Nine monosaccharides and ten disaccharides were evaluated as substrates for a fusion protein, which contains both alpha-(1 --> 3)-galactosyltransferase and uridine-5'-diphosphogalactose 4-epimerase. Four disaccharide and six trisaccharide alpha -Gal epitope derivatives were synthesized utilizing this novel fusion enzyme. (C) 2000 Elsevier Science Ltd. All rights reserved.