Methyl 3,4-di-O-acetyl-2-deoxy-2-iodo-β-D-ribo-pyranoside | 131267-52-2

• 英文名称: Methyl 3,4-di-O-acetyl-2-deoxy-2-iodo-β-D-ribo-pyranoside
• 英文别名: [(3R,4R,5R,6R)-4-acetyloxy-5-iodo-6-methoxyoxan-3-yl] acetate
• CAS: 131267-52-2
• 化学式: C₁₀H₁₅IO₆
• 分子量: 358.13
• InChiKey: FJTIVMVRDDYMJN-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-D-ribo-pyranoside 在 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以82%的产率得到Methyl 3,4-di-O-acetyl-2-deoxy-β-D-erythro-pentopyranoside
  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
• 作为产物：
  描述：

  甲醇 、 3,4-di-O-acetyl-D-arabinal 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 以39%的产率得到Methyl 3,4-di-O-acetyl-2-deoxy-2-iodo-β-D-ribo-pyranoside
  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

• Steric and conformational effects in the dehalogenation of 2-halo sugar derivatives with tributylstannane
  作者：Derek Horton、Waldemar Priebe、Marcos L. Sznaidman

  DOI：10.1021/jo00059a037

  日期：1993.3

  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.
• HORTON, DEREK;PRIEBE, WALDEMAR;SZNAIDMAN, MARCOS, CARBOHYDR. RES., 205,(1990) C. 71-86
  作者：HORTON, DEREK、PRIEBE, WALDEMAR、SZNAIDMAN, MARCOS

  DOI：——

  日期：——