1,3,4,6-四-O-乙酰基-2-脱氧-D-来苏-吡喃己糖 | 75828-75-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1,3,4,6-四-O-乙酰基-2-脱氧-D-来苏-吡喃己糖
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-deoxy-D-lyxo-hexopyranose
• 英文别名: 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-galactopyranose；[(2R,3R,4R)-3,4,6-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 75828-75-0
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: KLEORKVJPIJWNG-MVWAYNQESA-N

物化性质

• 沸点：
  401.1±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  1,3,4,6-四-O-乙酰基-2-脱氧-D-来苏-吡喃己糖 在 正丁基锂 、 溶剂黄146 作用下， 反应 21.25h， 生成 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl 1-O,O'-dibenzyl phosphate
  参考文献：
  名称：

  β-（1→4）-d-半乳糖基转移酶的供体底物UDP-2-脱氧-d-己糖己糖（“ UDP-2-脱氧-d-半乳糖”）的化学合成和动力学表征

  摘要：

  牛β-（1→4）-半乳糖基转移酶（GalT）将半乳糖从UDP-半乳糖转移至以β-D-GlcpNAc为末端的寡糖，以产生N-乙酰基乳糖胺序列。我们在这里报告了非常不稳定的UDP-2-脱氧-D-lyxo-己糖（“ UDP-2-脱氧-半乳糖，” 2）作为GalT的供体的化学合成，结构表征和酶促评估。当β-D-GlcpNAc-O（CH2）8COOMe被用作受体时，供体2的动力学参数包括Km值为51 microM，几乎与天然底物UDP-半乳糖的动力学参数相同。分离出酶促转移的产物，并确认其具有预期的2'-脱氧-N-乙酰基乳糖胺序列。

  DOI：

  10.1016/0008-6215(93)80066-n
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 氢溴酸 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 22.5h， 生成 1,3,4,6-四-O-乙酰基-2-脱氧-D-来苏-吡喃己糖
  参考文献：
  名称：

  Hydrolytic activity of α-galactosidases against deoxy derivatives of p-nitrophenyl α-d-galactopyranoside

  摘要：

  The four possible monodeoxy derivatives of p-nitrophenyl (PNP) alpha-D-galactopyranoside were synthesized, and hydrolytic activities of the alpha-galactosidase of green coffee bean, Mortierella vinacea and Aspergillus niger against them were elucidated. The 2- and 6-deoxy substrates were hydrolyzed by the enzymes from green coffee bean and M. vinacea, while they scarcely acted on the 3- and 4-deoxy compounds. On the other hand, A. niger alpha-galactosidase hydrolyzed only the 2-deoxy compound in these deoxy substrates, and the activity was very high. These results indicate that the presence of two hydroxyl groups (OH-3 and -4) is essential for the compounds to act as substrates for the enzymes of green coffee bean and M. vinacea, while the three hydroxyl groups (OH-3, -4, and -6) are necessary for the activity of the A. niger enzyme. The kinetic parameters (K-m and V-max) of the enzymes for the hydrolysis of PNP alpha-D-galactopyranoside and its deoxy derivatives were obtained from kinetic studies. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00281-5

文献信息

• Efficient Synthesis of 2-Deoxyglycosyl-1-<i>O</i>-Acyl Esters via 2-Deoxyglycosyl Phosphorodithioates as Glycosyl Donors
  作者：Joanna Borowiecka、Maria Michalska

  DOI：10.1055/s-1994-25554

  日期：——

  An efficient glycosylation of carboxylic acids 2a-p has been developed employing 2-deoxyglycosyl phosphorodithioates 1a-h as glycosyl donors and Ag+ salts as activators. In the case of aliphatic acids the method is highly β-stereoselective. Stereoselectivity of glycosylation of aromatic acids depends on their structure. The α/β ratio is temperature dependent. Hydroxy groups in α-hydroxycarboxylic acids are not affected by glycosylation under the reaction conditions used.

  利用2-脱氧糖基磷酸二硫酯1a-h作为糖基供体和Ag+盐作为活化剂，已经开发出一种高效的羧酸2a-p的糖基化方法。对于脂肪族酸，该方法具有高度的β-立体选择性。芳香族酸的糖基化立体选择性取决于其结构，α/β比例受温度影响。在所用的反应条件下，α-羟基羧酸中的羟基不受糖基化的影响。
• Immunostimulatory and Antitumor Activities of Monoglycosylceramides Having Various Sugar Moieties.
  作者：Kazuhiro MOTOKI、Masahiro MORITA、Eiichi KOBAYASHI、Takeshi UCHIDA、Kohji AKIMOTO、Hideaki FUKUSHIMA、Yasuhiko KOEZUKA

  DOI：10.1248/bpb.18.1487

  日期：——

  Ten kinds of monoglycosylceramides (MonoCers), having the same ceramide portion and different sugar moieties, were synthesized and their immunostimulatory and antitumor activities were examined. The manner of combination between sugar and ceramide has been demonstrated to affect the manifestation of immunostimulatory and resultant antitumor activities of MonoCers, and in the case of D-MonoCers having the D-sugar, α-D-MonoCers (sugar combined to ceramide in an α-configuration) show stronger activities than β-D-MonoCers. Furthermore, the form of sugar, not the furanose-form but the pyranose-form, and the 2''-and 4''-hydroxyl groups of the pyranose-form of sugar, seemed to play an important role in the manifestation of the activities of α-D-MonoCers.

  合成了十种单糖基神经酰胺（MonoCers），它们具有相同的神经酰胺部分和不同的糖基部分，并研究了它们的免疫刺激和抗肿瘤活性。糖与神经酰胺的结合方式已被证明会影响MonoCers的免疫刺激及其相应的抗肿瘤活性的表现。对于含有D-糖的D-MonoCers，α-D-MonoCers（糖以α-构型与神经酰胺结合）显示出比β-D-MonoCers更强的活性。此外，糖的形式，不是呋喃糖形式而是吡喃糖形式，以及吡喃糖形式的糖的2''和4''-羟基，似乎在α-D-MonoCers的活性表现中起着重要作用。
• Synthesis of Nonnatural Nucleoside Diphosphate Sugars
  作者：Saskia Wolf、Rosmirt Molina Berrio、Chris Meier

  DOI：10.1002/ejoc.201100906

  日期：2011.11

  an efficient chemical method for the synthesis of a variety of naturally occurring nucleoside diphosphate (NDP) sugars. This method, which is based on the cycloSal approach, can also be used, in principle, for the preparation of rare or even nonnatural NDP sugars. Herein, the syntheses of sulfoquinovose-, glucose-6-sulfate-, L-galactose-, and 2-fluoroglycopyranoside-containing NDP sugars are presented

  最近，我们报道了一种合成多种天然核苷二磷酸 (NDP) 糖的有效化学方法。这种基于 cycloSal 方法的方法原则上也可用于制备稀有甚至非天然 NDP 糖。在此，介绍了含有磺基奎诺糖、葡萄糖-6-硫酸盐、L-半乳糖和 2-氟吡喃糖苷的 NDP 糖的合成，以及具有非天然核苷的 NDP 糖的合成。所描述的反应以高产率和短反应时间提供立体异构定义的 NDP 糖。
• Thio-click reaction of 2-deoxy-<i>exo</i>-glycals towards new glycomimetics: stereoselective synthesis of <i>C</i>-2-deoxy-<scp>d</scp>-glycopyranosyl compounds
  作者：János József、László Juhász、László Somsák

  DOI：10.1039/c8nj06138f

  日期：——

  conditions. Photoinitiated thiol–ene additions of these exo-glycals resulted in the corresponding C-(2-deoxy-D-glycopyranosyl)methyl sulfides in medium to good yields with exclusive regio- and stereoselectivities in most cases. Several disaccharide mimics with a C–S moiety in place of the glycosidic oxygen were also obtained.

  一系列的2-脱氧吡喃葡萄糖基氰化物与d -阿拉伯糖，d -来苏，d -赤，和d -苏式构型，由相应的烯糖合成通过2-脱氧吡喃葡萄糖基乙酸盐。通过在甲苯磺酰肼存在下用NaH 2 PO 2 / Ra-Ni还原将氰化物转化为脱水醛糖甲苯磺酰hydr。在改良的Bamford–Stevens条件下，甲苯磺酰azo提供了2-deoxy- exo - glycals。这些外糖的光引发硫醇烯加成反应产生了相应的在大多数情况下，C-（2-脱氧-D-甘露糖基糖基）甲基硫化物具有中等至良好的收率，并且具有独特的区域选择性和立体选择性。还获得了几个具有C–S部分代替糖苷氧的二糖模拟物。
• Synthetic utility of 1,1,2,2-tetraaryldisilanes: radical reduction of alkyl phenyl chalcogenides
  作者：Osamu Yamazaki、Hideo Togo、Masataka Yokoyama

  DOI：10.1039/a905937g

  日期：——

  Reactivity of tetraaryldisilanes as radical reducing agents of alkyl phenyl chalcogenides initiated by Et3B or AIBN was studied. Here, the reactivity of alkyl sulfide was poor; however, various alkyl phenyl selenides and tellurides were reduced to the corresponding hydrocarbons in good yields with 1,1,2,2-tetraphenyldisilane.

  研究了由Et 3 B或AIBN引发的四芳基乙硅烷作为烷基苯基硫族化物自由基还原剂的反应性。在此，烷基硫化物的反应性差。但是，用1,1,2,2-四苯基乙硅烷可将各种烷基苯基硒化物和碲化物以良好的收率还原为相应的烃类。