2-deoxy-2-azido-3,4,6-tri-O-acetyl-α-D-galactopyranosyl iodide | 68733-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-deoxy-2-azido-3,4,6-tri-O-acetyl-α-D-galactopyranosyl iodide
• 英文别名: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl iodide；3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl iodide；[(2R,3R,4R,5R,6R)-3,4-diacetyloxy-5-azido-6-iodooxan-2-yl]methyl acetate
• CAS: 68733-27-7
• 化学式: C₁₂H₁₆IN₃O₇
• 分子量: 441.179
• InChiKey: JUWPYVJKIMHAEP-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-azido-3,4,6-tri-O-acetyl-α-D-galactopyranosyl iodide 在 4 A molecular sieve 、 四乙基氯化铵 作用下， 以 乙腈 为溶剂， 以70%的产率得到3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride
  参考文献：
  名称：

  The synthesis of derivatives of 3-O-(2-acetamido-2-deoxy-α-d-galacto-pyranosyl)-L-serine and-L-threonine

  摘要：

  DOI：

  10.1016/s0008-6215(00)85142-3
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl nitrate 生成 2-deoxy-2-azido-3,4,6-tri-O-acetyl-α-D-galactopyranosyl iodide
  参考文献：
  名称：

  LEMIEUX, R. U.;RATCLIFFE, R. M.

  摘要：

  DOI：

文献信息

• Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from
  申请人：Chembiomed Ltd.

  公开号：US04195174A1

  公开（公告）日：1980-03-25

  O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.

  O-乙酰化的糖醛与偏铈铵硝酸盐在存在硝酸钠的情况下反应，产生良好产率的O-乙酰化2-叠氮基-2-脱氧糖基硝酸盐。这些硝酸盐可用于制备2-氨基-2-脱氧糖类，如D-半乳糖胺和乳糖胺。O-乙酰化的2-叠氮基-2-脱氧糖基硝酸盐可被转化为O-乙酰化的2-叠氮基-2-脱氧糖基卤化物，这些卤化物在制备O-乙酰化的2-叠氮基-2-脱氧糖苷时很有用，而后者可以还原为2-氨基-2-脱氧糖苷。特别感兴趣的是合成对应于人类A血型抗原决定簇的2-氨基-2-脱氧糖苷。将这些糖苷连接到固定支持体上可提供有效地吸附血浆中的抗A抗体的免疫吸附剂。
• Synthesis of a common trisaccharide fragment of glycoforms of the outer core region of the Pseudomonas aeruginosa lipopolysaccharide
  作者：Bozhena S. Komarova、Yury E. Tsvetkov、Yuriy A. Knirel、Ulrich Zähringer、Gerald B. Pier、Nikolay E. Nifantiev

  DOI：10.1016/j.tetlet.2006.03.045

  日期：2006.5

  β-glucosylation of an α-(1→4)-linked Glc-GalN3 unit, did not lead to the target trisaccharide backbone. Further O-deacetylation, azido group reduction and debenzylation of the protected trisaccharide precursor gave the corresponding trisaccharide amine. The latter structure was used in the synthesis of a series of trisaccharides bearing an acetyl group, an l-alanine or an N-acetylated l-alanine residue

  报道了铜绿假单胞菌脂多糖外核心区糖型的常见三糖的首次合成。通过对β-（1→3）连接的6 - O-苄基-2-叠氮基-2-脱氧-3 - O -（- ）进行高效的α-（1→4）-葡萄糖基化反应，可以制备出具有完全保护作用的三糖前体。2,3,4,6-四-O-乙酰基-β-d-吡喃葡萄糖基）-α-d-吡喃半乳糖苷。相反，糖基化的替代序列涉及与α-（1→4）连接的Glc-GalN 3的β-糖基化单位，没有导致目标三糖骨架。被保护的三糖前体的进一步O-脱乙酰基，叠氮基还原和脱苄基反应得到相应的三糖胺。后一种结构用于合成一系列三糖，其在GalN的C-2的氨基上带有乙酰基，1-丙氨酸或N-乙酰化的1-丙氨酸残基。
• Mild Synthesis of Protected α-D-Glycosyl Iodides
  作者：Romualdo Caputo、Horst Kunz、Domenico Mastroianni、Giovanni Palumbo、Silvana Pedatella、Francesco Solla

  DOI：10.1002/(sici)1099-0690(199911)1999:11<3147::aid-ejoc3147>3.0.co;2-i

  日期：1999.11

  α-D-Glycosyl iodides are stereoselectively obtained by iodine replacement of the free anomeric hydroxyl group of fully protected sugars treated with a polymer bound triarylphosphane-iodine complex and imidazole. High yields and mild conditions, compatible with all the common protecting groups used in carbohydrate chemistry, characterize the conversion.

  α-D-糖基碘化物是通过碘取代用聚合物结合的三芳基膦-碘复合物和咪唑处理的完全保护的糖的游离异头羟基而立体选择性地获得的。与碳水化合物化学中使用的所有常见保护基团兼容的高产率和温和条件是转化的特征。
• Iodine Promoted Glycosylation with Glycosyl Iodides: α‐Glycoside Synthesis
  作者：Renate van Well、K. Ravindranathan Kartha、Robert Field

  DOI：10.1081/car-200067028

  日期：2005.8.1

  Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave a-glucoside selectively. Use of less reactive acceptors led to the formation of alpha/beta-mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded beta-glucosides only. In contrast, iodine-promoted glycosylation of serine and threonine with 2-azido-2-deoxy-glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only alpha-linked products in high yield in most cases.
• BEMILLER, JAMES N.;BLAZIS, VINCENT J.;MYERS, ROBERT W., J. CARBOHYDR. CHEM., 9,(1990) N, C. 39-57
  作者：BEMILLER, JAMES N.、BLAZIS, VINCENT J.、MYERS, ROBERT W.

  DOI：——

  日期：——