acetyl 3,4,6-tri-(O-benzyl)-2-deoxy-2-iodo-β-D-galactopyranoside | 202919-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: acetyl 3,4,6-tri-(O-benzyl)-2-deoxy-2-iodo-β-D-galactopyranoside
• 英文别名: [(2S,3R,4S,5S,6R)-3-iodo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] acetate
• CAS: 202919-84-4
• 化学式: C₂₉H₃₁IO₆
• 分子量: 602.466
• InChiKey: HJIZGFPKFGZUFJ-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  acetyl 3,4,6-tri-(O-benzyl)-2-deoxy-2-iodo-β-D-galactopyranoside 、 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 4,6-benzylidene-2-O-benzoyl-3-O-(3,4,6-tri-(O-benzyl)-2-deoxy-2-iodo-β-D-galactopyranosyl)-(1->3)-α-D-glucopyranoside 、 methyl 4,6-benzylidene-2-O-benzoyl-3-O-(3,4,6-tri-(O-benzyl)-2-deoxy-2-iodo-α-D-galactopyranosyl)-(1->3)-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of 2-Deoxy-β-Galactosides via 2-Deoxy-2-bromo- and 2-Deoxy-2-iodo-galactopyranosyl Donors

  摘要：

  A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors.

  DOI：

  10.1021/ol034393t
• 作为产物：
  描述：

  3,4,6-三邻苄基半乳醛 、 以 甲苯 为溶剂， 反应 72.0h， 生成 (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-iodotetrahydro-2H-pyran-2-yl acetate 、 acetyl 3,4,6-tri-(O-benzyl)-2-deoxy-2-iodo-β-D-galactopyranoside
  参考文献：
  名称：

  Phosphonium salts of diacetoxyiodine(I) anions, new reagents for the iodoacetoxylation of alkenes

  摘要：

  二乙酰氧基碘（I）阴离子 1 的新型鏻盐可与烯烃（如三-O-苄基半乳糖醛 8）结合，生成 1-乙酰氧基-2-碘吡喃糖 12a、b，可有效地用于合成 2-脱氧糖苷 14。

  DOI：

  10.1039/a706305i

文献信息

• Iodosobenzene diacetate-Iodine and IBX-Iodine: Reagent systems for the synthesis of diastereomerically enriched 2-deoxy-2-iodoglycosyl acetates and 2-deoxy-2-iodoglycosyl ortho-iodobenzoates from protected glycals
  作者：Puli Saidhareddy、Sama Ajay、Arun K. Shaw

  DOI：10.1016/j.tet.2017.06.001

  日期：2017.7

  stereoselective synthesis of trans-2-deoxy-2-iodoglycosylacetates and O-iodobenzoates respectively from differently protected glycals have been developed. They are compatible with a variety of protecting groups and various functional groups at 2C-position. Hexose-3,2-enolone 8 is obtained directly from 2-acetoxy glycal 5 by method A. An application to modified method B has been shown by synthesis of a diastereomerically

  两种有效的无金属试剂系统PhI（OAc）2 -I 2（方法A）和IBX-I 2（方法B），分别用于立体选择性地合成反式-2-脱氧-2-碘代糖基乙酸酯和O-碘代苯甲酸酯已经开发了保护的糖基。它们在2 C位与各种保护基和各种官能团相容。通过方法A直接从2-乙酰氧基乙二醇5获得己糖3,2-烯醇酮8。通过合成非对映体纯的α-糖基邻-己炔基苯甲酸酯12显示了对改良方法B的应用。从3,4,6-三糖供体ö乙酰基d-己烯糖在已在糖苷的合成被进一步利用两个步骤13 - 18。
• A simple, efficient alternative for highly stereoselective iodoacetoxylation of protected glycals
  作者：David W. Gammon、Henok H. Kinfe、Dirk E. De Vos、Pierre A. Jacobs、Bert F. Sels

  DOI：10.1016/j.tetlet.2004.10.166

  日期：2004.12

  yields and selectivities in less than 2 h at low temperatures to 2-deoxy-2-iodoglycosyl acetates using the simple, inexpensive reagent mixture of ammonium iodide, hydrogen peroxide and acetic anhydride/acetic acid in acetonitrile. The corresponding 2-deoxy-2-bromoglycosyl acetates are obtained using ammonium bromide instead of the iodide, although longer reaction times are required and selectivities are

  使用简单，廉价的碘化铵，过氧化氢和乙酸酐/乙酸在乙腈中的简单，廉价的试剂混合物，可以在低温下不到2小时的时间内，在不到2小时的时间内，高产率地将受保护的乙二醇转化为乙酸2-脱氧-2-碘代糖基乙酸酯。尽管需要更长的反应时间并且选择性差，但是使用溴化铵代替碘化物可获得相应的2-脱氧-2-溴糖基乙酸酯。