2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl azide | 158109-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl azide
• 英文别名: N-[(4aR,6R,7R,8R,8aS)-6-azido-8-hydroxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 158109-40-1
• 化学式: C₁₆H₂₀N₄O₆
• 分子量: 364.358
• InChiKey: ANWYDXZBRYGWHA-XDBIMZJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl azide 在 4 A molecular sieve 、 sodium cyanoborohydride 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2-acetamido-2-deoxy-6-O-(4-methoxybenzyl)-3-O-monochloroacetyl-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Stereoselective synthesis of glycosides and anomeric azides of glucosamine

  摘要：

  The beta-azide of O-acetyl protected N-acetyl glucosamine is efficiently accessible via a phase-transfer-catalyzed reaction of the corresponding glycosyl chloride with sodium azide. The azido group revealed to be a useful anomeric protection for modifications of the protecting group pattern of the glucosamine unit. Exchange of the O-acyl groups by 4-methoxybenzylidene and 4-methoxybenzyl (Mpm) protection delivered regioselectively blocked glucosaminyl azide derivatives. In contrast, the N-phthaloyl protected glucosaminyl azide was obtained quantitatively from the corresponding glycosyl fluoride via a boron trifluoride-promoted reaction with trimethylsilyl azide. N-Phthaloyl glucosaminyl fluoride was also revealed to be useful in the synthesis of beta-glucosamine glycosides and saccharides. Chitobiosyl azide 21 carrying a selectively removable 6-O-Mpm protection was synthesized from the O-acetyl protected N-phthaloyl glucosaminyl bromide and N-acetylglucosaminyl azide 13 as an acceptor selectively deblocked at O-4.

  DOI：

  10.1002/prac.19923340705
• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 、 2-乙酰氨基-2-脱氧-beta-d-吡喃葡萄糖叠氮化物 在 tetrafluoroboric acid 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以84%的产率得到2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Stereoselective synthesis of glycosides and anomeric azides of glucosamine

  摘要：

  The beta-azide of O-acetyl protected N-acetyl glucosamine is efficiently accessible via a phase-transfer-catalyzed reaction of the corresponding glycosyl chloride with sodium azide. The azido group revealed to be a useful anomeric protection for modifications of the protecting group pattern of the glucosamine unit. Exchange of the O-acyl groups by 4-methoxybenzylidene and 4-methoxybenzyl (Mpm) protection delivered regioselectively blocked glucosaminyl azide derivatives. In contrast, the N-phthaloyl protected glucosaminyl azide was obtained quantitatively from the corresponding glycosyl fluoride via a boron trifluoride-promoted reaction with trimethylsilyl azide. N-Phthaloyl glucosaminyl fluoride was also revealed to be useful in the synthesis of beta-glucosamine glycosides and saccharides. Chitobiosyl azide 21 carrying a selectively removable 6-O-Mpm protection was synthesized from the O-acetyl protected N-phthaloyl glucosaminyl bromide and N-acetylglucosaminyl azide 13 as an acceptor selectively deblocked at O-4.

  DOI：

  10.1002/prac.19923340705

文献信息

• METHOD OF COVALENTLY LINKING A CARBOHYDRATE OR POLYALKYLENE OXIDE TO A PEPTIDE, PRECURSORS FOR USE IN THE METHOD AND RESULTANT PRODUCTS
  申请人：MacMillan Derek

  公开号：US20100069607A1

  公开（公告）日：2010-03-18

  A glycopeptide of the formula S-L-X—P, wherein: S is selected from an optionally protected monosaccharide, an optionally protected polysaccharide, a polyalkylene oxide chain and a group of the formula II, wherein R 1 and R 3 are independently selected from H or Ac, R 4 is Ac, and R 2 is a group of formula IV, wherein R 7 and R 8 are each independently selected from an optionally protected monosaccharide and an optionally protected polysaccharide, A, B, C and D are each independently 1 or 2, and m is 1 to 5; -L- is a moiety of the formula III wherein R 5 and R 6 are independently selected from H and Me and n is 1 to 3; and P is a peptide chain containing at least one amino acid having on its side chain the atom X, wherein X is an oxygen, a sulphur atom or a —CH 2 — moiety.

  化合物为S-L-X—P的糖肽，其中：S选自可选择保护的单糖、可选择保护的多糖、聚烷氧基链和式II的基团，其中R1和R3各自独立地选自H或Ac，R4为Ac，R2为式IV的基团，其中R7和R8各自独立地选自可选择保护的单糖和可选择保护的多糖，A、B、C和D各自独立地为1或2，m为1到5；-L-为式III的基团，其中R5和R6各自独立地选自H和Me，n为1到3；P为含有至少一个侧链上有X原子的氨基酸的肽链，其中X为氧原子、硫原子或-CH2-基团。
• Synthesis of ?-fucosyl glycosides and disaccharides using 4-methoxybenzyl (Mpm) protected fucosyl donors
  作者：Horst Kunz、Carlo Unverzagt

  DOI：10.1002/prac.19923340706

  日期：——

  The 4-methoxybenzyl (Mpm) group removable by selective oxidation was applied as a non-neighbouring-group-active protection of fucose hydroxy functions in the stereoselective synthesis of alpha-fucosides of acceptors containing double bonds sensitive to hydrogenation. With this aim, the synthesis of the alpha-fucosyl chloride (4) carrying the acid-sensitive Mpm protection was elaborated.
• US5874411A
  申请人：——

  公开号：US5874411A

  公开（公告）日：1999-02-23