1-S-(-2-carboxamido)methyl-1-deoxy-1-thio-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose | 1058155-77-3

• 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-S-(-2-carboxamido)methyl-1-deoxy-1-thio-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-amino-2-oxoethyl)sulfanyloxan-2-yl]methyl acetate
• CAS: 1058155-77-3
• 化学式: C₁₆H₂₃NO₁₀S
• 分子量: 421.425
• InChiKey: KQIQGAYZDZVMJV-JZYAIQKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  183
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-S-(-2-carboxamido)methyl-1-deoxy-1-thio-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 在 Oxone 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以33%的产率得到1-S-(-2-carboxamido)methyl-1-deoxy-1-sulfinyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  Hydrogen bonding in crystal forms of primary amide functionalised glucose and cellobiose

  摘要：

  A glucoside and cellobioside of glycolamide were synthesised and the crystal chemistry of these compounds investigated. The amidoglucoside crystallised in the P2(1) space group. The primary amide group participates in C(7) and C(17) chains also involving the pyranose oxygen and hydroxyl groups. The amidocellobioside crystallised as a methanol solvate in the P2(1) space group. The amide N-H groups donate hydrogen bonds to oxygen atoms on the cellobiose units, while intramolecular hydrogen bonds give rise to S(7) and S(9) motifs in addition to a R-3(3) (9) motif. A tetra-O-acetylglucoside derivative of thioglycolamide and its sulfoxide derivative were synthesised to examine the effect of protecting the glucopyranose hydroxyl groups. The thioglycolamido derivative, which crystallised in the P2(1)2(1)2(1) space group, featured amide N-H groups donating to the glucopyranose oxygen and an acetyloxy group. The sulfoxy derivative crystallised in the P2(1) space group and featured the primary amide groups forming R-2(3)(8) motifs generating a 2(1) ladder. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.024
• 作为产物：
  描述：

  氯乙酰胺 、 β-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 、 硫脲 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以48%的产率得到1-S-(-2-carboxamido)methyl-1-deoxy-1-thio-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  Hydrogen bonding in crystal forms of primary amide functionalised glucose and cellobiose

  摘要：

  A glucoside and cellobioside of glycolamide were synthesised and the crystal chemistry of these compounds investigated. The amidoglucoside crystallised in the P2(1) space group. The primary amide group participates in C(7) and C(17) chains also involving the pyranose oxygen and hydroxyl groups. The amidocellobioside crystallised as a methanol solvate in the P2(1) space group. The amide N-H groups donate hydrogen bonds to oxygen atoms on the cellobiose units, while intramolecular hydrogen bonds give rise to S(7) and S(9) motifs in addition to a R-3(3) (9) motif. A tetra-O-acetylglucoside derivative of thioglycolamide and its sulfoxide derivative were synthesised to examine the effect of protecting the glucopyranose hydroxyl groups. The thioglycolamido derivative, which crystallised in the P2(1)2(1)2(1) space group, featured amide N-H groups donating to the glucopyranose oxygen and an acetyloxy group. The sulfoxy derivative crystallised in the P2(1) space group and featured the primary amide groups forming R-2(3)(8) motifs generating a 2(1) ladder. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.024

文献信息

• Synthesis and evaluation of antitubercular activity of glycosyl thio- and sulfonyl acetamide derivatives
  作者：Samir Ghosh、Pallavi Tiwari、Shashi Pandey、Anup Kumar Misra、Vinita Chaturvedi、Anil Gaikwad、Shalini Bhatnagar、Sudhir Sinha

  DOI：10.1016/j.bmcl.2008.06.004

  日期：2008.7

  A series of glycosyl thioacetamide and glycosyl sulfonyl acetamide derivatives have been prepared following a convenient reaction protocol and evaluated for their antitubercular activity against Mycobacterium tuberculosis H(37)Rv. Amongst 32 compounds evaluated 3 compounds were effective in inhibiting mycobacterial growth at MIC of 6.25 mu g/mL, 6 compounds at MIC of 3.125 mu g/mL and 1 compound at MIC of 1.56 mu g/mL. All active compounds were found nontoxic in Vero cell lines and mice bone marrow macrophages. (c) 2008 Elsevier Ltd. All rights reserved.
• Hydrogen bonding in crystal forms of primary amide functionalised glucose and cellobiose
  作者：Humphrey A. Moynihan、John A. Hayes、Kevin S. Eccles、Simon J. Coles、Simon E. Lawrence

  DOI：10.1016/j.carres.2013.03.024

  日期：2013.6

  A glucoside and cellobioside of glycolamide were synthesised and the crystal chemistry of these compounds investigated. The amidoglucoside crystallised in the P2(1) space group. The primary amide group participates in C(7) and C(17) chains also involving the pyranose oxygen and hydroxyl groups. The amidocellobioside crystallised as a methanol solvate in the P2(1) space group. The amide N-H groups donate hydrogen bonds to oxygen atoms on the cellobiose units, while intramolecular hydrogen bonds give rise to S(7) and S(9) motifs in addition to a R-3(3) (9) motif. A tetra-O-acetylglucoside derivative of thioglycolamide and its sulfoxide derivative were synthesised to examine the effect of protecting the glucopyranose hydroxyl groups. The thioglycolamido derivative, which crystallised in the P2(1)2(1)2(1) space group, featured amide N-H groups donating to the glucopyranose oxygen and an acetyloxy group. The sulfoxy derivative crystallised in the P2(1) space group and featured the primary amide groups forming R-2(3)(8) motifs generating a 2(1) ladder. (C) 2013 Elsevier Ltd. All rights reserved.