methyl 3,4-di-O-acetyl-2-deoxy-2-iodo-β-L-fucopyranoside | 72864-51-8

• 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-deoxy-2-iodo-β-L-fucopyranoside
• 英文别名: [(2S,3R,4R,5S,6S)-4-acetyloxy-5-iodo-6-methoxy-2-methyloxan-3-yl] acetate
• CAS: 72864-51-8
• 化学式: C₁₁H₁₇IO₆
• 分子量: 372.157
• InChiKey: NDZIEVXADQZATG-NNGJRSOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-acetyl-2-deoxy-2-iodo-β-L-fucopyranoside 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72%的产率得到methyl 3,4-di-O-acetyl-2,6-dideoxy-β-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
• 作为产物：
  描述：

  甲醇 、 2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 在 碘 、 silver(I) acetate 作用下， 反应 1.0h， 以64%的产率得到methyl 3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-talopyranoside
  参考文献：
  名称：

  吗啡的约14个β取代的类似物的合成和止痛活性。

  摘要：

  用硼氢化钠处理14β-硝基可待因酮得到可待因衍生物，其在乙酸酐-乙酸溶液中用锌粉还原，得到14β-乙酰氨基可待因6-乙酸盐。从蒂巴因与硫氰酸根的反应获得14β-硫氰基可待因酮，并用氢化铝锂将其还原为14β-巯基可待因。通过蒂巴因分别与N-溴代琥珀酰亚胺和N-氯代琥珀酰亚胺反应，制备了14个β-溴-和14个-氯可待因酮。用三溴化硼将这14个β-取代的可待因和可待因酮O-去甲基化为相应的吗啡类似物。除了活性较弱的14个β-硝基吗啡酮外，

  DOI：

  10.1021/jm00176a011

文献信息

• Iodoalkoxylation of 1,5-anhydro-2-deoxy-hex-1-enitols (glycals)
  作者：Derek Horton、Waldemar Priebe、Marcos Sznaidman

  DOI：10.1016/0008-6215(90)80129-q

  日期：1990.9

  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.