ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside | 312967-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-5-amino-6-ethylsulfanyl-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 312967-20-7
• 化学式: C₈H₁₇NO₄S
• 分子量: 223.293
• InChiKey: VJOYNADMAQNGBK-PVFLNQBWSA-N

物化性质

• 沸点：
  439.4±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 水 、 碳酸氢铵 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 4.0h， 生成 2-乙酰氨基-1-氨基-1,2-二脱氧-beta-D-吡喃葡萄糖
  参考文献：
  名称：

  From Glycals to Glycopeptides: A Convergent and Stereoselective Total Synthesis of a High Mannose N-Linked Glycopeptide

  摘要：

  DOI：

  10.1002/1521-3773(20001016)39:20<3652::aid-anie3652>3.0.co;2-b
• 作为产物：
  描述：

  4-O-Acetyl-3,6-di-O-benzyl-D-glucal 在 bisdicollidine iodonium perchloride 、 氨 、 sodium 作用下， 生成 ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  From Glycals to Glycopeptides: A Convergent and Stereoselective Total Synthesis of a High Mannose N-Linked Glycopeptide

  摘要：

  DOI：

  10.1002/1521-3773(20001016)39:20<3652::aid-anie3652>3.0.co;2-b

文献信息

• Sweets for Catalysis - Facile Optimisation of Carbohydrate-Based Bis(oxazoline) Ligands
  作者：Tobias Minuth、Mustafa Irmak、Annika Groschner、Tobias Lehnert、Mike M. K. Boysen

  DOI：10.1002/ejoc.200801035

  日期：2009.3

  A new type of carbohydrate-based bis(oxazoline) ligands was prepared from inexpensive D-glucosamine and tested in asymmetric cyclopropanation reactions. For optimisation, modified ligands with 3-O substituents of varying size and electronic properties were prepared as well as a 3-OH unprotected and a perpivaloylated derivative. All new ligands were tested in asymmetric cyclopropanation, revealing a

  一种新型的基于碳水化合物的双（恶唑啉）配体由廉价的 D-葡糖胺制备，并在不对称环丙烷化反应中进行了测试。为了优化，制备了具有不同大小和电子特性的 3-O 取代基的修饰配体以及未保护的 3-OH 和全新戊酰化衍生物。所有新配体都在不对称环丙烷化中进行了测试，揭示了对映选择性对 3-O 残基的空间需求和电子特性的强烈依赖性。此外，观察到由环状缩醛基团的存在或不存在决定的吡喃糖构象的显着影响。因此，很容易将新的碳水化合物双（恶唑啉）配体调整到给定的反应。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）
• Design and synthesis of novel cell wall inhibitors of Mycobacterium tuberculosis GlmM and GlmU
  作者：Yongmeng Li、Yan Zhou、Yufang Ma、Xuebing Li

  DOI：10.1016/j.carres.2011.05.024

  日期：2011.9

  GlmM and GlmU are key enzymes in the biosynthesis of UDP-N-acetyl-D-glucosamine (UDP-GlcNAc), an essential precursor of peptidoglycan and the rhamnose-GlcNAc linker region in the mycobacterial cell wall. These enzymes are involved in the conversion of two important precursors of UDP-GlcNAc, glucosamine-6-phosphate (GlcN-6-P) and glucosamine-1-phosphate (GlcN-1-P). GlmM converts GlcN-6-P to GlcN-1-P, GlmU is a bifunctional enzyme, whereby GlmU converts GlcN-1-P to GlcNAc-1-P and then catalyzes the formation of UDP-GlcNAc from GlcNAc-1-P and uridine triphosphate. In the present study, methyl 2-amino-2-deoxyl-alpha-D-glucopyranoside 6-phosphate (1 alpha), methyl 2-amino-2deoxyl-beta-D-glucopyranoside 6-phosphate (1 beta), two analogs of GlcN-6-P, were synthesized as GlmM inhibitors; 2-azido-2-deoxy-alpha-D-glucopyranosyl phosphate (2) and 2-amino-2,3-dideoxy-3-fluoro-alpha-Dglucopyranosyl phosphate (3), analogs of GlcN-1-P, were synthesized firstly as GlmU inhibitors. Compounds 1 alpha, 1 beta, 2, and 3 as possible inhibitors of mycobacterial GlmM and GlmU are reported herein. Compound 3 showed promising inhibitory activities against GlmU, whereas 1 beta, 1 beta and 2 were inactive against GlmM and GlmU even at high concentrations. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• Facile preparation of glycosyl donors for oligosaccharide synthesis: 2-azido-2-deoxyhexopyranosyl building blocks
  作者：Therese Buskas、Per J. Garegg、Peter Konradsson、Jean-Luc Maloisel

  DOI：10.1016/s0957-4166(00)86294-1

  日期：1994.11

  Facile routes to the 2-azido-2-deoxy-1-thioglycosides 6, 7, 15, and 18 and of the 2-azido-2-deoxy-4-pentenoglycoside 11, are described. These are useful intermediates for the synthesis of oligo-saccharides containing alpha-D-2-amino-2-deoxy (or 2-acetamido-2-deoxy) hexosyl residues in the galacto-, gluco-, and manno- series.
• Investigations of Glycosylation Reactions with 2-<i>N</i>-Acetyl-2<i>N</i>,3<i>O</i>-oxazolidinone-Protected Glucosamine Donors
  作者：Johan D. M. Olsson、Lars Eriksson、Martina Lahmann、Stefan Oscarson

  DOI：10.1021/jo800971s

  日期：2008.9.19

  NIS/AgOTf-promoted glycosylations with ethyl 2,3-N,O-carbonyl-2-deoxy-1-thio-beta-D-glueopyranoside donors can be performed with either alpha- or beta-selectivity by tuning the reaction conditions. Small amounts of AgOTf (0.1 equiv) and short reaction times give beta-selectivity, whereas 0.4 equiv of AgOTf and prolonged reaction times afford alpha-linked products. NMR-monitored glycosylation and anomerization experiments show initial formation of exclusively the beta-linkage, which anomerizes, through an intramolecular mechanism involving an endocyclic C - O bond cleavage, to the alpha-linkage.