Methyl 3,4-di-O-acetyl-2,6-dideoxy-2-iodo-β-L-gluco-pyranoside | 131267-43-1

• 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-2-iodo-β-L-gluco-pyranoside
• 英文别名: [(2S,3S,4R,5S,6S)-4-acetyloxy-5-iodo-6-methoxy-2-methyloxan-3-yl] acetate
• CAS: 131267-43-1
• 化学式: C₁₁H₁₇IO₆
• 分子量: 372.157
• InChiKey: NDZIEVXADQZATG-HRVYYWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 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-2-iodo-β-L-gluco-pyranoside 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75%的产率得到methyl-3,4-di-O-acetyl-2,6-didesoxy-β-L-arabino-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
• 作为产物：
  描述：

  甲醇 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 以60%的产率得到methyl-3,4-diacetyl-2,6-dideoxy-2-iodo-α-L-manno-hexopyranoside
  参考文献：
  名称：

  Iodoalkoxylation of 1,5-anhydro-2-deoxy-hex-1-enitols (glycals)

  摘要：

  Exclusive trans-addition is observed in the iodoalkoxylation of the 6-membered cyclic enol ethers 3,4-di-O-acetyl-L-rhamnal (1), 3,4-di-O-acetyl-L-fucal (2), and related glycal derivatives. The main products from 1 and from 3,4,6-tri-O-acetyl-D-glucal (3) thus had the alpha-manno configuration. Similarly, alpha-talo products were obtained from 2 in 87-93% yield. The product distribution is not affected by the electronegativity of the 5-substituent. It is concluded that steric factors in the glycal and the nucleophile affect only the step of trans-diaxial opening of the intermediate iodonium ion. Enhanced yields of the desired trans-diaxial products were observed in reactions of glycals having the lyxo configuration when the reactions were conducted in tetrahydrofuran or methanol.

  DOI：

  10.1016/0008-6215(90)80129-q

文献信息

• Radical oxygenation of 2-deoxy-2-iodo hexopyranosides with molecular oxygen
  作者：Stéphane Moutel、Jacques Prandi

  DOI：10.1016/0040-4039(94)88272-x

  日期：1994.10

  2-Deoxy-2-iodo hexopyranosides react with molecular oxygen and tributylstannane to give the epimeric C-2 alcohols in high yield and moderate selectivity.

  2-脱氧-2-碘六吡喃糖苷与分子氧和三丁基锡烷反应，以高收率和适度的选择性产生差向异构的C-2醇。