benzyl 2-azido-3-O-benzyl-2-deoxy-α-D-manofuranoside | 1332835-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-azido-3-O-benzyl-2-deoxy-α-D-manofuranoside
• CAS: 1332835-24-1
• 化学式: C₂₀H₂₃N₃O₅
• 分子量: 385.42
• InChiKey: JCVQYBYRLRAVEE-IVDHNXQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  116.91
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-azido-3-O-benzyl-2-deoxy-α-D-manofuranoside 在 吡啶 、 sodium hydride 、 二正丁基氧化锡 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 26.33h， 生成 benzyl 2-N-acetyl-3,6-di-O-benzyl-2-deoxy-5-O-methyl-α-D-mannofuranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of C8-modified sialic acids and related α2–3- and α2–6-linked sialosides

  摘要：

  Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 ( PmNanA). In addition, alpha 2-3- and alpha 2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.083
• 作为产物：
  描述：

  benzyl 3-O-benzyl-5,6-carbonate-α-D-glucofuranoside 在 吡啶 、 sodium azide 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 benzyl 2-azido-3-O-benzyl-2-deoxy-α-D-manofuranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of C8-modified sialic acids and related α2–3- and α2–6-linked sialosides

  摘要：

  Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 ( PmNanA). In addition, alpha 2-3- and alpha 2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.083

文献信息

• Synthesis of N-acetylmannosamine-6-phosphate derivatives to investigate the mechanism of N-acetylmannosamine-6-phosphate 2-epimerase
  作者：Tanzeel Arif、Michael J. Currie、Renwick C.J. Dobson、Harriet L. Newson、Vivek Poonthiyil、Antony J. Fairbanks、Rachel A. North、Phillip M. Rendle

  DOI：10.1016/j.carres.2021.108445

  日期：2021.12