2-deoxy-2-azido-3,4,6-tri-O-acetyl-α-D-galactopyranose | 71906-78-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-azido-3,4,6-tri-O-acetyl-α-D-galactopyranose
• 英文别名: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranose；3,4,6-Tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranose；3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactose；3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranose；(2R,3R,4R,5R)-2-(acetoxymethyl)-5-azido-6-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate；3,4,6-tri-O-acetyl-2-deoxy-2-azido-D-galactopyranose；[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-hydroxyoxan-2-yl]methyl acetate
• CAS: 71906-78-0
• 化学式: C₁₂H₁₇N₃O₈
• 分子量: 331.282
• InChiKey: PLVPDCSPQJIUQM-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-azido-3,4,6-tri-O-acetyl-α-D-galactopyranose 在 咪唑 、 triphenylphospine diiodide 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以90%的产率得到2-deoxy-2-azido-3,4,6-tri-O-acetyl-α-D-galactopyranosyl iodide
  参考文献：
  名称：

  受保护的 α-D-糖基碘化物的温和合成

  摘要：

  α-D-糖基碘化物是通过碘取代用聚合物结合的三芳基膦-碘复合物和咪唑处理的完全保护的糖的游离异头羟基而立体选择性地获得的。与碳水化合物化学中使用的所有常见保护基团兼容的高产率和温和条件是转化的特征。

  DOI：

  10.1002/(sici)1099-0690(199911)1999:11<3147::aid-ejoc3147>3.0.co;2-i
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-deoxy-2-azido-3,4,6-tri-O-acetyl-α-D-galactopyranose
  参考文献：
  名称：

  Paulsen,H.; Sumfleth,B., Chemische Berichte, 1979, vol. 112, p. 3203 - 3213

  摘要：

  DOI：

文献信息

• Solution and Solid-Phase Stereocontrolled Synthesis of 1,2-<i>cis</i>-Glycopyranosides with Minimally Protected Glycopyranosyl Donors Catalyzed by BF₃–<i>N</i>,<i>N</i>-Dimethylformamide Complex
  作者：Gabrielle St-Pierre、Stephen Hanessian

  DOI：10.1021/acs.orglett.6b01263

  日期：2016.7.1

  Methods are described for the stereoselective synthesis of 1,2-cis glycopyranosides in the d-galacto, d-gluco, and 2-azido-2-deoxy-d-glucopyranoside series utilizing minimally protected (3-bromo-2-pyridyloxy) β-d-glycopyranosyl donors in the presence of BF3–N,N-dimethylformamide (DMF) as a catalyst and a variety of alcohol acceptors relying on the “remote activation concept”. Precursors to antifreeze

  方法的1,2-立体选择性合成中描述的顺式glycopyranosides在d半乳，d -gluco和2-叠氮基-2-脱氧d吡喃葡萄糖苷系列利用所最低限度地受保护的（3-溴-2-吡啶基氧基）β - d在BF的存在-glycopyranosyl供体3 - ñ，ñ-二甲基甲酰胺（DMF）作为催化剂和多种醇受体，依赖于“远程活化概念”。抗冻糖肽组分的前体以优异的产率和高的α/β比率合成。该方法适用于一锅顺序糖苷化反应以及固相支持的合成方法，从而可以得到各种主要保护的最低限度保护的α- d-吡喃葡萄糖苷类化合物。
• Use of Hydrazine Acetate as a Mild and Efficient Reagent for Anomeric Denitration of Carbohydrates
  作者：Tatsushi Toyokuni、Shaopei Cai、Barbara Dean

  DOI：10.1055/s-1992-26347

  日期：——

  Treatment of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α,β-D-galactopyranosyl nitrate (1), 3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4, 6-tetra-O-acetyl-β-D-galactopyranosyl)-α,β-D-glucopyranosyl nitrate (3), and 6-O-acetyl-2-azido-2-deoxy-3,4-O-isopropylidene-α,β-D-galactopyranosyl nitrate (5) with a slight excess of hydrazine acetate in anhydrous dimethylformamide at room temperature for 2 hours gave the corresponding hemiacetals, 2, 4, and 6 in the range of an 87-92 % yield.

  将 3,4,6-三-O-乙酰基-2-叠氮-2-脱氧-δ±,δ-D-吡喃半乳糖硝酸酯 (1)、3,6-二-O-乙酰基-2-叠氮-2-脱氧-4-O-(2,3,4, 6-四-O-乙酰基-δ-D-吡喃半乳糖基)-δ±,δ-D-吡喃葡萄糖硝酸酯 (3) 和 6-O-乙酰基-2-叠氮-2-脱氧-3、在室温下，在无水二甲基甲酰胺中加入稍过量的乙酸肼 2 小时，再加入 4-O-异亚丙基-δ,δ-D-吡喃半乳糖基硝酸酯（5），得到相应的半乙酸酯 2、4 和 6，收率范围为 87-92%。
• Synthesis of N1-(p-glycosyloxycinnamoyl)spermidines
  作者：Yoshihiro Saito、Tsuyoshi Watanabe、Hironobu Hashimoto、Juji Yoshimura

  DOI：10.1016/0008-6215(87)80249-5

  日期：1987.11

  Abstract The synthesis of O -glycosylated N 1 -( p -hydroxycinnamoyl)spermidines was investigated. p -Hydroxycinnamate glycosides of some amino sugars, including a synthetic intermediate of a unique antibiotic, cinodine, were prepared and converted into the amide of spermidine.

  摘要研究了O-糖基化的N 1-（对羟基肉桂酰基）亚精胺的合成。制备了一些氨基糖的对羟基肉桂酸酯糖苷，包括独特的抗生素西诺定的合成中间体，并将其转化为亚精胺的酰胺。
• Efficient Synthesis of Azido Sugars Using Fluorosulfuryl Azide Diazotransfer Reagent**
  作者：Joshua M. Kofsky、Gour C. Daskhan、Matthew S. Macauley、Chantelle J. Capicciotti

  DOI：10.1002/ejoc.202200108

  日期：2022.8.5

  An operationally simple protocol for diazotransfer on amine-containing carbohydrates has been developed. This high-yielding reaction can be conducted under ambient conditions. Reaction completion is indicated by the colour change of the Cu(II) catalyst. The utility of this protocol in chemical glycosylation has been demonstrated through the preparation of azide-containing glycosyl donors with orthogonal

  已开发出一种操作简单的含胺碳水化合物重氮转移方案。这种高产反应可以在环境条件下进行。反应完成由 Cu(II) 催化剂的颜色变化指示。该协议在化学糖基化中的效用已通过制备具有正交保护基团的含叠氮化物糖基供体得到证明。
• Stereoselective entry into the d-GalNAc series starting from the d-Gal one: a new access to N-acetyl-d-galactosamine and derivatives thereof
  作者：Lorenzo Guazzelli、Giorgio Catelani、Felicia D’Andrea、Alessia Giannarelli

  DOI：10.1016/j.carres.2008.11.018

  日期：2009.2

  A new stereoselective preparation of N-aceyl-D-galactosamine (1b) starting from the known p-methoxyphenyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-beta-D-galactopyranoside (10) is described using a simple strategy based on (a) epimerization at C-2 of 10 via oxidation-reduction to give the talo derivative 11, (b) amination with configurational inversion at C-2 of 11 via a S(N)2-type reaction

  从已知的对甲氧基苯基3,4-O-异亚丙基-6-O-（1-甲氧基-1-甲基乙基）-β-D-吡喃半乳糖苷（使用基于（a）通过氧化还原在C-2处10的差向异构化得到滑石衍生物11（b）通过S（N）在C-2处11的构型反转的胺化的简单策略来描述10）在其2-亚酰胺基上进行2型反应，（c）对甲氧基苯基β-D-半乳糖胺糖苷14的端基异构脱保护，（d）完全脱保护。将相同的方法应用于通过以下方法直接获得的2,3：5,6：3'，4'-三-O-异亚丙基-6'-O-（1-甲氧基-1-甲基乙基）-乳糖二甲基乙缩醛（4）乳糖的乙酰化，二糖β-D-GalNAcp-（1->