allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranoside | 63064-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)-2-prop-2-enoxyoxan-3-yl]acetamide
• CAS: 63064-53-9
• 化学式: C₂₅H₃₁NO₆
• 分子量: 441.524
• InChiKey: LNVLLAQPQDEPBC-JYSSUKAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranoside 在 三氟化硼乙醚 、 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.67h， 生成 allyl 2-acetylamino-2-deoxy-3,4-dibenzyl-6-O-(3,4-O-dibenzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Studies on carbohydrates XVIII. Synthesis of tetrasaccharide corresponding to biological repeat units of Serratia marcescens O18 polysaccharide

  摘要：

  The sqnthesis of a blocked tetrasaccharide portion of the biological repeat unit, [-->2)L-Rhap alpha(1-->2)L-Rhap alpha(1-->2)L-Rhap alpha (1-->6)D-GlcNAcp alpha(1-->], of the Serratia marcescens O18 polysaccharide was described The key intermediate compounds was 3,4-blocked -L-rhamnose. All compounds were confirmed by use of high resolution NMR and FAB-MS techniques.

  DOI：

  10.1016/s0957-4166(00)86306-5
• 作为产物：
  描述：

  allyl 2-acetamido-2-deoxy-3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 sodium cyanoborohydride 作用下， 生成 allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Side products of glycosidation with selected 2-acetamido-2-deoxy-d-glucopyranosides

  摘要：

  Allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-formyl-alpha-D-glucopyranoside, N-acetyl-2,3,4-tri-O-acetyl-L-fucopyranosylamine and products of O-acetyl group migration were found as side products during glycosidation of selected 2-acetamido-2-deoxy-D-glucopyranosides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00207-0

文献信息

• Synthesis and Properties of Surfactants derived from<i>N</i>‐Acetyl‐<scp>D</scp>‐Glucosamine
  作者：Chadi Khoury、Michel Minier、François Le Goffic、Marie‐Noëlle Rager

  DOI：10.1080/07328300701634804

  日期：2007.10

  The synthesis of 2-acetamido-2-deoxy-6-O-octanoyl-D-glucono-1,5-lactone 9 and 2-acetamido-2-deoxy-6-O-octanoyl-alpha-D-glueopyranose 7 from 2-acetamido-2-deoxy-alpha-D-glucopyranose is reported. For both targets, the key intermediate was allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-octanoyl-alpha-D-glucopyranoside 5. Surface tension measurements (critical micellar concentration of 22.3 mM and 5 mM for 9 and 7, respectively) showed up the surface activity of both compounds, while enzyme inhibition assays indicated that 9 could inhibit bovine beta-N-acetylglucosaminidase (K-i = 6.5 mu M) but not Serratia marcescens chitobiase nor hen egg-white lysozyme. Moreover, 7 was shown to induce chitinase production of S. marcescens and to be readily metabolized by these bacteria.[GRAPHICS]