2-allylphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside | 1370590-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-allylphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-prop-2-enylphenoxy)oxane
• CAS: 1370590-24-1
• 化学式: C₄₃H₄₄O₆
• 分子量: 656.819
• InChiKey: ZCGAQOTVPCYFBJ-FYYRRIAOSA-N

物化性质

• 沸点：
  742.1±60.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-allylphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 在 palladium 10% on activated carbon 、 氢气 、 silver trifluoromethanesulfonate 、 一氯化碘 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 18.0h， 生成
  参考文献：
  名称：

  2-Allylphenyl glycosides as glycosyl donors for sugar coupling

  摘要：

  Glycosylations employing 2-allylphenyl glycoside, a new type of stable glycosyl donor, were optimized and explored with a variety of acceptors promoted by ICl/AgOTf. The utility of the protocol was further demonstrated with an efficient synthesis of the disaccharide fragment of bleomycins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.022
• 作为产物：
  描述：

  2-allylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 14.0h， 生成 2-allylphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  2-Allylphenyl glycosides as glycosyl donors for sugar coupling

  摘要：

  Glycosylations employing 2-allylphenyl glycoside, a new type of stable glycosyl donor, were optimized and explored with a variety of acceptors promoted by ICl/AgOTf. The utility of the protocol was further demonstrated with an efficient synthesis of the disaccharide fragment of bleomycins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.022

文献信息

• One-Pot Anti-Markovnikov Hydroamination of Unactivated Alkenes by Hydrozirconation and Amination
  作者：Alexandra E. Strom、John F. Hartwig

  DOI：10.1021/jo401498w

  日期：2013.9.6

  A one-pot anti-Markovnikov hydroamination of alkenes is reported. The synthesis of primary and secondary amines from unactivated olefins was accomplished in the presence of a variety of functional groups. Hydrozirconation, followed by amination with nitrogen electrophiles, provides exclusive anti-Markovnikov selectivity. Most products are isolated in high yields without the use of column chromatography

  报道了烯烃的一锅抗马尔科夫尼科夫加氢胺化反应。由未活化烯烃合成伯胺和仲胺是在各种官能团的存在下完成的。氢化锆，然后用氮亲电试剂胺化，提供独特的抗马尔科夫尼科夫选择性。大多数产品以高产率分离，无需使用柱层析。