十六烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷 | 115414-47-6

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 十六烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷
• 英文名称: hexadecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-Acetamido-3,4-diacetyloxy-6-hexadecoxyoxan-2-yl]methyl acetate
• CAS: 115414-47-6
• 化学式: C₃₀H₅₃NO₉
• 分子量: 571.752
• InChiKey: IQLBKMQSMVEUHD-XZTOTZIXSA-N

物化性质

• 沸点：
  656.1±55.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  40
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  十六烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷 在 硫酸 、 sodium methylate 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 hexadecyl 2-acetamido-4,6-O-benzylidene-3-O-(D-1-carboxyethyl)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of glycosidic analogues of N-acetylneuramoyl-L-alanyl-D-isoglutamine

  摘要：

  DOI：

  10.1007/bf00598682
• 作为产物：
  描述：

  1-十六烷醇 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 3 A molecular sieve 、 mercury(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 以61%的产率得到十六烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷
  参考文献：
  名称：

  Synthesis of?-glycosides of n-acetylglucosamine in the presence of HgI2

  摘要：

  DOI：

  10.1007/bf01372338

文献信息

• Synthesis of Oligosaccharides Designed to form Micelles, Corresponding to Structures Found in Ovarian Cyst Fluid
  作者：Therese Buskas、Peter Konradsson

  DOI：10.1080/07328300008544063

  日期：2000.1

  The syntheses of alpha-D-GlcpNAc-(1-->4)-beta-D-Galp-(1-->4)-beta-D-GlcNAc-(1-->O)-(CH2)(15)CH3 (1) and fragments thereof, corresponding to structures found in human ovarian cyst fluid, are described. Silver triflate promoted coupling of 3.4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranosyl bromide (12) and galactose acceptor (11) gave a disaccharide donor (13), which was readily transformed into the corresponding bromo-derivative 18. For the synthesis of disaccharide beta-D-Galp-(1-->4)-D-GlcNAc, several differently protected glucosamine accepters were prepared. It was found that cetyl alcohol needed to be introduced after the formation of the P-galactoside bond. Glycosylation of pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (30) with (3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-alpha-D-galactopyranosyl bromide (18) by use of silver triflate as promoter gave the desired trisaccharide 31. Finally 31 was transformed via coupling to the long alkyl chain aglycon and deprotection into the title compound 1.
• Preparation of ether-linked 2-acetamido-2-deoxy β-glycolipids via zinc chloride promoted coupling of Ac4GlcNAcCl with lipid hydroxy groups
  作者：Erukulla Ravi Kumar、Hoe-Sup Byun、Sihe Wang、Robert Bittman

  DOI：10.1016/s0040-4039(00)75823-0

  日期：1994.1

  Stereoselective glycosidation of lipid hydroxy groups has been achieved using 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glycosyl chloride as the glycosyl donor in CH2Cl2. In the presence of ZnCl2 (1 equiv.) and various ''promoters'' (1 equiv.) such as Ph(3)CCl, 18-crown-6/KCl, n-Bu(4)NBr, or Me(3)SiCl, beta-glycolipid conjugates are formed as the initial products, but they undergo anomerization on prolonged reaction times. The promoters may enhance the solubility of ZnCl2 in CH2Cl2.