methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranoside | 78464-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranoside
• 英文别名: Methyl-3,4-di-O-acetyl-2-desoxy-α-L-fucopyranosid；methyl 2-deoxy-3,4-di-O-acetyl-α-L-fucopyranoside；methyl 2,6-dideoxy-3,4-di-O-acetyl-α-L-lyxohexopyranoside；[(2S,3R,4S,6R)-3-acetyloxy-6-methoxy-2-methyloxan-4-yl] acetate
• CAS: 78464-95-6
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: YYOUDJJKCIBTNG-BOWGKDCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranoside 在 barium dihydroxide 、 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 23.0h， 生成 2,6-dideoxy-L-ribo-α-pyranose
  参考文献：
  名称：

  Alternative syntheses of 2,6-dideoxy-l-lyxo-hexose (2-deoxy-l-fucose) and itsbiochemical properties

  摘要：

  DOI：

  10.1016/s0008-6215(82)80020-7
• 作为产物：
  描述：

  methyl 3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-talopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以80%的产率得到methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  Steric and conformational effects in the dehalogenation of 2-halo sugar derivatives with tributylstannane

  摘要：

  The stereochemistry of dehalogenation of 2-halo sugars with tributyltin hydride has been investigated in terms of the influence of steric and conformational effects using deuterium-labeling techniques. Detailed analysis of the results (Tables I-III) demonstrates that the size and orientation of the ring substituents are a determining factor in the stereochemical outcome of the reaction' However, some results can only be explained considering reduction of two equilibrating radical conformers.

  DOI：

  10.1021/jo00059a037

文献信息

• Stoffwechselprodukte von Mikroorganismen. 202. Mitteilung. Strukturaufklärung von Elaiophylin: Spektroskopische Untersuchungen und Abbau
  作者：Hanspeter Kaiser、Walter Keller-Schierlein

  DOI：10.1002/hlca.19810640206

  日期：1981.3.18

  Structure Elucidation of Elaiophylin: Spectroscopy and Chemical Degradation

  Elaiophylin的结构阐明：光谱学和化学降解
• Anomeric activation of thioglycosides and preparation of deoxyglycosides using polymer-bound iodate(I) complexes
  作者：Janis Jaunzems、Georgia Sourkouni-Argirusi、Martin Jesberger、Andreas Kirschning

  DOI：10.1016/s0040-4039(02)02708-9

  日期：2003.1

  New thiophilic polymer-bound haloate(l) complexes are presented which are well suited for the polymer-assisted solution-phase activation of 2-deoxythioglycosides. In the presence of alcohols 2-deoxyglycosides are obtained in yields between 60 and 95%. Isolation of the target glycosides is further simplified by removing the byproduct diphenyldisulfide by reductive work-up. Here also a polymer-bound reagent, namely borohydride exchange resin, served as a tool for sequestering the sulfur-containing impurities. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of 2-deoxy sugars from glycals
  作者：Subramaniam Sabesan、Susana Neira

  DOI：10.1021/jo00018a054

  日期：1991.8
• US5128463A
  申请人：——

  公开号：US5128463A

  公开（公告）日：1992-07-07