1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose | 16750-07-5

• 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
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose
• 英文别名: 1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-arabino-hexopyranose；2-deoxy-β-D-arabino-hexopyranose tetraacetate；Tetra-O-acetyl-2-desoxy-β-D-glucopyranose；1,3,4,6-tetra-O-acetyl-2-desoxy-beta-d-arabino-hexopyranose；[(2R,3S,4R,6S)-3,4,6-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 16750-07-5
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: KLEORKVJPIJWNG-SYQHCUMBSA-N

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

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到2-Deoxy-D-glucose
  参考文献：
  名称：

  A convenient synthesis of 2-deoxy-d-arabino-hexose and of its methyl and benzyl glycosides

  摘要：

  DOI：

  10.1016/s0008-6215(00)81880-7
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以65%的产率得到1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Giese, Bernd; Gilges, Stefan; Groeninger, Kay S., Liebigs Annalen der Chemie, 1988, p. 615 - 617

  摘要：

  DOI：

文献信息

• A Novel Approach for the Formation of Carbon−Nitrogen Bonds:  Azidation of Alkyl Radicals with Sulfonyl Azides
  作者：Cyril Ollivier、Philippe Renaud

  DOI：10.1021/ja004129k

  日期：2001.5.1

  Two preparatively attractive methods for the azidation of alkyl radicals are described. Secondary and tertiary alkyl iodides and dithiocarbonates are easily converted into the corresponding azides, either by reaction with ethanesulfonyl azide in the presence of dilauroyl peroxide, or by treatment with benzenesulfonyl azide and hexabutylditin in the presence of a radical initiator. Interestingly, intramolecular

  描述了用于烷基基团叠氮化的两种制备性有吸引力的方法。通过在过氧化二月桂酰存在下与乙磺酰叠氮化物反应，或在自由基引发剂存在下用苯磺酰叠氮化物和六丁基二锡处理，仲和叔烷基碘和二硫代碳酸酯很容易转化为相应的叠氮化物。有趣的是，分子内串联自由基环化-叠氮化过程可以以高产率进行。
• Direct Deamination of Primary Amines via Isodiazene Intermediates
  作者：Kathleen J. Berger、Julia L. Driscoll、Mingbin Yuan、Balu D. Dherange、Osvaldo Gutierrez、Mark D. Levin

  DOI：10.1021/jacs.1c09779

  日期：2021.10.27

  here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition

  我们在这里报告了一种在温和条件下选择性地脱氨基伯胺和苯胺的反应，并且具有显着的官能团耐受性，包括一系列药物化合物、氨基酸、氨基糖和天然产物。端基异构酰胺试剂能够通过前所未有的单取代异二氮烯中间体作为中介促进反应。与现有协议相比，除了显着简化脱氨之外，我们的方法还可以将亚胺和胺导向化学作为无痕方法进行战略应用。机械和计算研究支持初级异二氮的中间作用，它与以前研究的次级异二氮表现出意想不到的差异，导致逃逸笼子的自由基物种参与链，
• Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions
  作者：Jing Fang、Ting Li、Xiang Ma、Jiuchang Sun、Lei Cai、Qi Chen、Zhiwen Liao、Lingkui Meng、Jing Zeng、Qian Wan

  DOI：10.1016/j.cclet.2021.06.069

  日期：2022.1

  The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of

  描述了一种在无过渡金属条件下参与烷基化和芳基化的锍叶立德。不同的反应模式允许单独激活非叶立基S-烷基和S-芳基键。在酸性条件下，锍叶立德用作促进烷基化的烷基阳离子前体。而在碱性条件下，非叶立基 S-芳基键的断裂可有效地产生O-芳基化化合物。协议的稳健性是由包括碳水化合物在内的各种底物的出色兼容性建立的。
• 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。
• A Novel Stereoselective Synthesis of S-Glycosyl Phosphorodithioates from Peracetylated Sugars
  作者：Wiestawa Kudelska、Maria Michalska

  DOI：10.1055/s-1995-4435

  日期：1995.12

  The reaction of per-O-acetylated mono- and disaccharides 1a-1l with free O,O-dialkylphosphorodithioic acid 2a, its S-trimethylsilyl ester 2b or its trialkylammonium salt 2c in the presence of boron trifluoride-diethyl ether complex affords per-O-acetylglycosyl phosphorodithioates in high yields and stereoselectivity.

  在三氟化硼-二乙醚复合物的存在下，全-O-乙酰化的单糖和双糖1a-1l与自由的O,O-二烷基次膦酸酯2a、其S-三甲基硅基酯2b或其三烷基铵盐2c反应，可高产率且立体选择性地生成全-O-乙酰基糖磷硫酸酯。