2-acetamido-3,4,6-tri-O-acetyl-1-N-(chloroacetyl)-2-deoxy-β-D-glucopyranosylamine | 73982-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-1-N-(chloroacetyl)-2-deoxy-β-D-glucopyranosylamine
• 英文别名: 2-Acetamido-3,4,6-tri-O-acetyl-N-chloroacetyl-2-deoxy-β-D-glucopyranosylamine；N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)chloroacetamide；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2-chloroacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 73982-38-4
• 化学式: C₁₆H₂₃ClN₂O₉
• 分子量: 422.82
• InChiKey: SYAJXVMCKPCXFN-JPIRQXTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-1-N-(chloroacetyl)-2-deoxy-β-D-glucopyranosylamine 在 sodium azide 、 palladium on activated charcoal 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 48.0h， 生成 1-N-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-N''-(n-octyl)thioureidoacetamide
  参考文献：
  名称：

  硫脲和脲连接的糖脂作为低分子量水凝胶剂的合成与表征†

  摘要：

  通过使糖基氨基乙酰胺与烷基异硫氰酸酯和异氰酸酯反应，已经合成了具有硫脲和脲连接基的新型糖脂作为低分子量胶凝剂。研究了连接基团对其自组装性能的影响。对获得的新糖脂在各种溶剂中的胶凝研究表明，它们是良好的水凝剂。与硫脲连接的糖脂相比，尿素连接的糖脂显示出更好的水凝胶化能力。还研究了糖首基和烷基链长对糖脂自组装的影响。超分子水凝胶的原纤维结构已经通过扫描电子显微镜（SEM）表征。由尿素连接的糖脂形成的水凝胶的热性质已通过差示扫描量热法（DSC）和VT-NMR进行了研究。已经通过小角度（SAXS）和单晶X射线衍射方法研究了分子堆积。

  DOI：

  10.1039/c3ra42041h
• 作为产物：
  描述：

  2-乙酰氨基-1-氨基-1,2-二脱氧-beta-D-吡喃葡萄糖 在 Na β-zeolite 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2-acetamido-3,4,6-tri-O-acetyl-1-N-(chloroacetyl)-2-deoxy-β-D-glucopyranosylamine
  参考文献：
  名称：

  Synthesis ofN‐(β‐Glycopyrano‐syl)azidoacetamides

  摘要：

  N-(beta-Glycopyranosyl)azidoacetamides, mimetics of the widely distributed GlcNAc-Asn linkage in glycoproteins, have been synthesized in good yields starting from beta-glycopyranosylamines in four steps involving selective N-chloroacetylation, peracetylation catalyzed by Na beta-zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de-O-acetylation.

  DOI：

  10.1081/car-200049402

文献信息

• Synthesis and biological activity of some 1-N-substituted 2-acetamido-2-deoxy-β-d-glycopyranosylamine derivatives and related analogs
  作者：Brajeswar Paul、Ralph J. Bernacki、Walter Korytnyk

  DOI：10.1016/s0008-6215(00)85318-5

  日期：——

  adenocarcinoma TA3, leukemia L1210, or leukemia P-288 cells at 1-0.01 mM concentration in vitro. Some of these derivatives were less active after O-deacetylation. Analogs of 1 in which NH2-1 was replaced by OH- or OAc-1 were also active on the same cell systems. The growth-inhibitory activity was correlated with inhibition of the incorporation of 2-amino-deoxy-D-glucose and L-leucine into a macromolecular fraction

  2-乙酰氨基-2-脱氧-3,4,6-三-O的几种1-N-取代的衍生物[卤代乙酰基，甘氨酰-，（二甲基）氨基-乙酰基，叠氮基乙酰基，三氟乙酰基和三氟甲基磺酰基-] -乙酰基-β-D-吡喃葡萄糖胺（1）被合成为细胞膜糖缀合物的潜在代谢抑制剂。在体外浓度为1-0.01 mM时，发现几种完全乙酰化的衍生物可以抑制小鼠乳腺腺癌TA3，白血病L1210或白血病P-288细胞的生长。这些衍生物中的一些在O-脱乙酰基之后活性较低。其中NH2-1被OH-或OAc-1取代的类似物1在相同的电池系统上也很活跃。生长抑制活性与2-氨基-脱氧-D-葡萄糖和L-亮氨酸掺入大分子级分的抑制有关。
• Efficient One-pot Syntheses of Chloroacetyl and <i>S</i>-Acetylmercaptoacetyl <i>N</i>-Glycosides from Glycosyl Azides
  作者：Juan García-López、Francisco Santoyo-González、Antonio Vargas-Berenguel

  DOI：10.1055/s-1997-775

  日期：1997.3

  Two convenient methods for the one-pot synthesis of chloroacetyl and S-acetylmercaptoacetyl N-glycosides from glycosyl azides have been developed. Both methods involve a mild reduction of the azido group using n-Bu3-P and 1,3-propanedithiol as reducing reagents, respectively.

  我们开发出了两种方便的方法，可从糖基叠氮化物中一次性合成氯乙酰基和 S-乙酰基巯基 N-糖苷。这两种方法分别使用正-Bu3-P 和 1,3-丙二硫醇作为还原剂，温和地还原叠氮基团。
• A novel strategy toward the synthesis of N-(β-glycosyl)asparagines based on the alkylation of ethyl nitroacetate using N-(β-glycosyl)iodoacetamides
  作者：Katuri J.V. Paul、Laxminarayan Sahoo、Duraikkannu Loganathan

  DOI：10.1016/j.tetlet.2010.08.072

  日期：2010.10

  A conceptually novel strategy has been developed for the synthesis of N-(β-glycosyl)asparagine precursors in good yield by the alkylation of ethyl nitroacetate using six per-O-acetylated N-(β-glycosyl)iodoacetamides derived from mono- and disaccharides. The use of a chiral organocatalyst, N-(9-anthracenylmethyl)cinchoninium chloride (10 mol %), resulted in diastereoselective alkylation up to 64% de

  已经开发了一种概念上新颖的策略，用于通过使用六种衍生自单糖和二糖的过氧乙酰化N-（β-糖基）碘乙酰胺对硝基乙酸乙酯进行烷基化，以高收率合成N-（β-糖基）天冬酰胺前体。。使用手性有机催化剂，N-（9-蒽基甲基）辛基氯化铵（10mol％），导致高达64％de的非对映选择性烷基化。对Glc衍生物的纯化的主要非对映异构体的单晶结构分析显示，在作为L-天冬酰胺缀合物的前体的单取代的硝基乙酸乙酯的α-碳上，S的绝对构型。
• SnCl4/Sn catalyzed chemoselective reduction of glycopyranosyl azides for the synthesis of diversely functionalized glycopyranosyl chloroacetamides
  作者：Laxminarayan Sahoo、Anadi Singhamahapatra、Katuri J.V. Paul、Duraikkannu Loganathan

  DOI：10.1016/j.tetlet.2013.07.110

  日期：2013.9

  A method for the chemoselective reduction of glycopyranosyl azides using SnCl4 and tin metal as the reducing agent followed by in situ chloroacetylation of the synthesized glycopyranosyl amine was developed. This reaction is applicable to diversely functionalized glycopyranosyl azides for the synthesis of glycopyranosyl chloroacetamides. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of ClusterN-Glycosides Based on aβ-Cyclodextrin Core
  作者：Juan J. García-López、Francisco Santoyo-González、Antonio Vargas-Berenguel、Juan J. Giménez-Martínez

  DOI：10.1002/(sici)1521-3765(19990604)5:6<1775::aid-chem1775>3.0.co;2-2

  日期：1999.6.4

  A convenient method for the synthesis of beta-D-gluco-, beta-D-galacto-, 2-acetamido-2-deoxy-beta-D-gluco- and alpha-D-mannopyranosylamine clusters based on cyclomaltoheptaose (beta-cyclodextrin) is presented. The synthesis involves: 1) the one-pot synthesis of the acetylated chloroacetyl N-glycoside derivatives of D-glucose, D-galactose, 2-acetamido-2-deoxy-D-glucose and D-mannose from the corresponding glycosyl azides, 2) conversion of the chloroacetyl N-glycosides into their isothiouronium derivatives, then 3) attachment of the N-glycosides onto heptakis(6-deoxy-6-iodo) and heptakis(6-chloroacetamido-6-deoxy) beta-cyclodextrin by means of nucleophilic displacement with caesiurn carbonate in dimethylformamide, and 4) de-O-acetylation of beta-cyclodextrin derivatives. The chloroacetyl N-glycoside derivatives were easily prepared by mild reduction of the azide function by one of two methods: a) by the Staudinger reaction, with nBu(3)P, and b) with 1,3-propanedithiol, as reducing reagents.