Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(2S,3S,4S,5R,6R)-6-allyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-carbamoyl-4-carbamoyloxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester | 193223-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(2S,3S,4S,5R,6R)-6-allyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-carbamoyl-4-carbamoyloxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester
• CAS: 193223-19-7
• 化学式: C₃₀H₄₉N₃O₁₅Si
• 分子量: 719.816
• InChiKey: PKDMOTJDHQYSSP-SOQHCROVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  49.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  249.56
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(2S,3S,4S,5R,6R)-6-allyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-carbamoyl-4-carbamoyloxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester 在 铜 、 乙酰丙酮 、 锌 作用下， 以 吡啶 为溶剂， 反应 1.0h， 生成 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-O-tert-butyldimethylsilyl-3-O-carbamoyl-1-O-{[(R)-2-methoxycarbonyl-2-(3,8,8,11,14,18-hexamethylnonadecyloxy)-ethoxy]-hydroxyphosphoryl}-α-D-glucopyranuronamide
  参考文献：
  名称：

  A Moenomycin-type Structural Analogue of Lipid II some possible mechanisms of the mode of action of transglycosylase inhibitors can be discarded

  摘要：

  The transglycosylation step in the peptidoglycan biosynthesis belongs to the general class of glycosyltransferase-catalyzed reactions. The structural analogue 2 of moenomycin A has been synthesized and has been found to be antibiotically inactive. The assumption that moenomycin-type transglycosylase inhibitors such as 1 bind at the donor site of the enzyme and that their mode of action is the result of the high stability of the sugar --> phosphate bond seems to be ruled out by the present results.

  DOI：

  10.1002/prac.19973390162
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2S,3R,4S,5R,6R)-6-allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-carbamoyl-tetrahydro-pyran-3-yloxy]-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.67h， 生成 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(2S,3S,4S,5R,6R)-6-allyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-carbamoyl-4-carbamoyloxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  A Moenomycin-type Structural Analogue of Lipid II some possible mechanisms of the mode of action of transglycosylase inhibitors can be discarded

  摘要：

  The transglycosylation step in the peptidoglycan biosynthesis belongs to the general class of glycosyltransferase-catalyzed reactions. The structural analogue 2 of moenomycin A has been synthesized and has been found to be antibiotically inactive. The assumption that moenomycin-type transglycosylase inhibitors such as 1 bind at the donor site of the enzyme and that their mode of action is the result of the high stability of the sugar --> phosphate bond seems to be ruled out by the present results.

  DOI：

  10.1002/prac.19973390162