methyl 4,6-di-O-acetyl-3-azido-2,3-dideoxy-β-D-xylo-hexopyranoside | 501091-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-di-O-acetyl-3-azido-2,3-dideoxy-β-D-xylo-hexopyranoside
• 英文别名: [(2R,3R,4S,6R)-3-acetyloxy-4-azido-6-methoxyoxan-2-yl]methyl acetate
• CAS: 501091-44-7
• 化学式: C₁₁H₁₇N₃O₆
• 分子量: 287.272
• InChiKey: ZEIDDKDESUEWSM-LNFKQOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4,6-di-O-acetyl-3-azido-2,3-dideoxy-β-D-xylo-hexopyranoside 在 吡啶 、 silver fluoride 、 sodium iodide 作用下， 以 吡啶 、 二氯甲烷 、 丙酮 为溶剂， 生成 methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-α-L-threo-hex-5-enopyranoside
  参考文献：
  名称：

  Synthesis and conformational studies on methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-hex-5-enopyranosides of the l series

  摘要：

  Methyl 3-azido-2,3-dideoxy-alpha-(D)-xylo-, -alpha-(D)-lyxo-, and -beta-(D)-xylo-hexopyranosides were converted into 4-O-acetyl-3azido-6-iodo-2,3,6-trideoxy analogues via 6-O-p-tolylsulfonyl compounds. The elimination of hydrogen iodide from 6-iodo glycosides yielded methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-beta-(L)-erythro-, -alpha-(L)-threo-, and -beta-(L)-threo-hex-5-enopyranosides. The configuration and conformation of all products are evaluated in depth on the basis of H-1 and C-13 NMR data. Factors determining conformational energy in 4- O-protected- 3 -azido-2,3,6,-trideoxy-hex-5-enopyrano sides are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.019
• 作为产物：
  描述：

  D-三乙酰半乳糖烯 在 2,4,6-三甲基吡啶 、 oxonium 、 汞 、 甲基磺酰氯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 methyl 4,6-di-O-acetyl-3-azido-2,3-dideoxy-β-D-xylo-hexopyranoside
  参考文献：
  名称：

  The use of tri-O-acetyl-d-glucal and -d-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides

  摘要：

  Addition of hydrazoic acid to alpha, beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the H-1 and C-13 NMR, IR and polarimetric data. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00288-4