octyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside | 219825-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside
• 英文别名: octyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-D-mannopyranoside；[(2R,3R,4S,5S,6S)-3,4-diacetyloxy-5-iodo-6-octoxyoxan-2-yl]methyl acetate
• CAS: 219825-30-6
• 化学式: C₂₀H₃₃IO₈
• 分子量: 528.382
• InChiKey: RCPIXRMXJQRYEH-IVDHNXQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  octyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以84%的产率得到octyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Iodoacetoxylation Reaction: A Convenient Route to α-Glycosides in the 2-Iodo and 2-Deoxy Series

  摘要：

  Iodoacetoxylation of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (tri-O-acetyl-D-glucal)(1) and 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (di-O-acetyl-L-rhamnal) (3) gave the alpha-1,2-trans-1-O-acetyl-2-deoxy-2-iodo adducts with high stereoselectivities and good yields, in accordance with the results reported on 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arahino-hex-1-enitol (hexa-O-acetyl lactal) (2). The alpha-1,2-trans adducts were reacted with an excess of alcohol in the presence of trimethylsilyl trifluoromethanesulfonate affording the corresponding alpha-1,2-trans-2-deoxy-2-iodo-glycopyranoside in good yields. The octyl 2-deoxy-2-iodo-alpha-D-glycosides 10 and 11 prepared in two steps from the glycals 1 and 2 were deiodinated and deacetylated, giving 28 and 29, and the physicochemical-properties (cmc) of 29 are reported.

  DOI：

  10.1080/07328309808002360
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 copper diacetate 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 octyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside
  参考文献：
  名称：

  Iodoacetoxylation Reaction: A Convenient Route to α-Glycosides in the 2-Iodo and 2-Deoxy Series

  摘要：

  Iodoacetoxylation of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (tri-O-acetyl-D-glucal)(1) and 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (di-O-acetyl-L-rhamnal) (3) gave the alpha-1,2-trans-1-O-acetyl-2-deoxy-2-iodo adducts with high stereoselectivities and good yields, in accordance with the results reported on 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arahino-hex-1-enitol (hexa-O-acetyl lactal) (2). The alpha-1,2-trans adducts were reacted with an excess of alcohol in the presence of trimethylsilyl trifluoromethanesulfonate affording the corresponding alpha-1,2-trans-2-deoxy-2-iodo-glycopyranoside in good yields. The octyl 2-deoxy-2-iodo-alpha-D-glycosides 10 and 11 prepared in two steps from the glycals 1 and 2 were deiodinated and deacetylated, giving 28 and 29, and the physicochemical-properties (cmc) of 29 are reported.

  DOI：

  10.1080/07328309808002360

文献信息

• An efficient method for the selective synthesis of 2-deoxy-2-iodo-glycosides by O-glycosidation of d-glucal using I2–Cu(OAc)2
  作者：Uthaiwan Sirion、Sittidate Purintawarrakun、Poolsak Sahakitpichan、Rungnapha Saeeng

  DOI：10.1016/j.carres.2010.08.020

  日期：2010.11

  An efficient and convenient method for the synthesis of 2-deoxy-2-iodo-O-glycosides from tri-O-acetyl-D-glucal with various alcohols by using I(2)-Cu(OAc)(2) is described. The 21 examples of corresponding glycosides were obtained in high yields, with good anomeric selectivity.

  描述了一种有效便捷的方法，可使用I（2）-Cu（OAc）（2）从三-O-乙酰基-D-葡萄糖与各种醇类合成2-脱氧-2-碘-O-糖苷。以高产率获得具有良好异头异构体选择性的21个相应糖苷实例。
• Convertible Formation of Different Glycoside Using Molecular Iodine
  作者：Rungnapha Saeeng、Uthaiwan Sirion、Yada Sirichan、Thanida Trakulsujaritchok、Poolsak Sahakitpichan

  DOI：10.3987/com-10-12043

  日期：——

  The observation of convertible formation between 2-deoxy-2-iodo-O-glycosides and 2,3-unsaturated glycoside was described. The selective formation of 2-deoxy-2-iodo-O-glycosides was found from the reaction of D-glucal with iodine in the excess alcohol acceptor or the addition of ceric ammonium nitrate as additive while the addition of a stoichiometric amount of alcohol in solvent favored 2,3-unsaturated glycosides formation.