2,3,4,6-tetra-O-acetyl-1-O-(N-allyl)carbamoyl-α-D-galactopyranose | 150630-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-1-O-(N-allyl)carbamoyl-α-D-galactopyranose
• CAS: 150630-98-1
• 化学式: C₁₈H₂₅NO₁₁
• 分子量: 431.397
• InChiKey: HRMJWHHRWONLBK-DRRXZNNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-1-O-(N-allyl)carbamoyl-α-D-galactopyranose 在 乙酸肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 2,3,4-tri-O-acetyl-6-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-α/β-D-glucopyranose
  参考文献：
  名称：

  Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-Allylcarbamates

  摘要：

  Glycosyl-N-allyl carbamates, obtained by reaction of anomerically unprotected saccharides with allyl isocyanate, can be activated by an electrophile-induced cyclisation and reacted with glycosyl accepters to form the corresponding oligosaccharides. By this method the mucin core 2 trisaccharide(2) has successfully been synthesized. Due to the mild glycosylation conditions even 1-O-acetyl protected glycosyl accepters can be used. This was demonstrated in the synthesis of a 1,6-linked glucosyl trisaccharide whereby a reptitious glycosylation strategy could be applied.

  DOI：

  10.1080/07328309808002350
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 乙酸肼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2,3,4,6-tetra-O-acetyl-1-O-(N-allyl)carbamoyl-α-D-galactopyranose
  参考文献：
  名称：

  Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-Allylcarbamates

  摘要：

  Glycosyl-N-allyl carbamates, obtained by reaction of anomerically unprotected saccharides with allyl isocyanate, can be activated by an electrophile-induced cyclisation and reacted with glycosyl accepters to form the corresponding oligosaccharides. By this method the mucin core 2 trisaccharide(2) has successfully been synthesized. Due to the mild glycosylation conditions even 1-O-acetyl protected glycosyl accepters can be used. This was demonstrated in the synthesis of a 1,6-linked glucosyl trisaccharide whereby a reptitious glycosylation strategy could be applied.

  DOI：

  10.1080/07328309808002350

文献信息

• Glycoside synthesis via electrophile-induced activation of N-allyl carbamates
  作者：Horst Kunz、Jörg Zimmer

  DOI：10.1016/s0040-4039(00)60478-1

  日期：1993.4

  O-Benzyl-, O-acyl-, N-acyl- and isopropylidene-protected glycosyl N-allylcarbamates, obtained from anomerically unprotected monosaccharides and allyl isocyanate, are activated by an electrophile-induced cyclisation and react with hydroxyl compounds to form the corresponding glycosides.

  由未保护的单糖和异氰酸烯丙酯得到的O-苄基，O-酰基，N-酰基和异亚丙基保护的糖基N-烯丙基氨基甲酸酯，通过亲电试剂诱导的环化反应活化，并与羟基化合物反应形成相应的糖苷。
• Synthesis of N-unsubstituted, mono- and disubstituted carbohydrate-1-O-carbamates and their behaviour in glycoside syntheses
  作者：Hans-Peter Knoben、Urs Schlüter、Hartmut Redlich

  DOI：10.1016/j.carres.2004.10.002

  日期：2004.12

  different 1-O-unprotected carbohydrate derivatives (compounds 1-6), representing typical protecting pattern in glycoside synthesis, are described. The carbamate function is N-unsubstituted (compounds 1b-6b), mono- (compounds a: N-trichloroacetyl, c: N-monochloroacetyl, d: N-acetyl, e: N-ethyl, f: N-allyl, g: N-phenyl) or disubstituted (compounds h: imidazolyl, i: N-diethyl, j: N-diphenyl). Additionally

  描述了由六个不同的1-O-未保护的碳水化合物衍生物（化合物1-6）合成的44个1-氨基甲酸酯，它们代表糖苷合成中的典型保护方式。氨基甲酸酯官能团是N-未取代的（化合物1b-6b），单-（化合物a：N-三氯乙酰基，c：N-一氯乙酰基，d：N-乙酰基，e：N-乙基，f：N-烯丙基，g： N-苯基）或二取代的（化合物h：咪唑基，i：N-二乙基，j：N-二苯基）。另外，合成了三种N-氯磺酰基氨基甲酸酯，并用作合成N-未取代的化合物b的中间体。描述并比较了这些化合物的可及性。一些氨基甲酸酯（1、4、5a-j）用作模型化合物，可用于糖苷合成的系统研究。选定的实验数据（反应条件，端基异构体比例，旋转值，