methyl 5-O-benzyl-2-cyclohexylamino-2,3-dideoxy-3-C-(p-tolylsulfonyl)-β-D-arabinofuranoside | 1038619-78-1

• 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: methyl 5-O-benzyl-2-cyclohexylamino-2,3-dideoxy-3-C-(p-tolylsulfonyl)-β-D-arabinofuranoside
• 英文别名: cHexNH(-2d)[Tos(-3d)][Bn(-5)]b-D-Araf1Me；(2R,3R,4S,5R)-N-cyclohexyl-2-methoxy-4-(4-methylphenyl)sulfonyl-5-(phenylmethoxymethyl)oxolan-3-amine
• CAS: 1038619-78-1
• 化学式: C₂₆H₃₅NO₅S
• 分子量: 473.634
• InChiKey: WMDHFFZXHPNVAX-XDZVQPMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  82.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-O-benzyl-2-cyclohexylamino-2,3-dideoxy-3-C-(p-tolylsulfonyl)-β-D-arabinofuranoside 在 magnesium 、 nickel dibromide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以67%的产率得到methyl 5-O-benzyl-2-cyclohexylamino-2,3-dideoxy-β-D-threo-pentofuranoside
  参考文献：
  名称：

  Unusual addition of amines to C-2 of vinyl sulfone-modified-β-d-pent-2-enofuranosyl carbohydrates: synthesis of a new class of β-anomeric 2-amino-2,3-dideoxy-d-threo-pentofuranosides

  摘要：

  When 3-C-sulfonyl-pent-2-enofuranosides and 3-C-sulfonyl-hex-2-enofuranosides were reacted with primary and secondary amines, only the beta-anomeric methoxy group of the pent-2-enofuranoside did not cause any hindrance to incoming nitrogen nucleophiles. This resulted in the 'unusual' addition of amines, in which the diastereoselectivity of the reaction was overwhelmingly in favor of amino sugars of the D-arabino configuration. Selected products were desulfonylated to obtain a new class of beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.03.022
• 作为产物：
  描述：

  环己胺 、 methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside 以80%的产率得到methyl 5-O-benzyl-2-cyclohexylamino-2,3-dideoxy-3-C-(p-tolylsulfonyl)-β-D-arabinofuranoside
  参考文献：
  名称：

  Unusual addition of amines to C-2 of vinyl sulfone-modified-β-d-pent-2-enofuranosyl carbohydrates: synthesis of a new class of β-anomeric 2-amino-2,3-dideoxy-d-threo-pentofuranosides

  摘要：

  When 3-C-sulfonyl-pent-2-enofuranosides and 3-C-sulfonyl-hex-2-enofuranosides were reacted with primary and secondary amines, only the beta-anomeric methoxy group of the pent-2-enofuranoside did not cause any hindrance to incoming nitrogen nucleophiles. This resulted in the 'unusual' addition of amines, in which the diastereoselectivity of the reaction was overwhelmingly in favor of amino sugars of the D-arabino configuration. Selected products were desulfonylated to obtain a new class of beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.03.022

文献信息

• Unusual addition of amines to C-2 of vinyl sulfone-modified-β-d-pent-2-enofuranosyl carbohydrates: synthesis of a new class of β-anomeric 2-amino-2,3-dideoxy-d-threo-pentofuranosides
  作者：Indrajit Das、Cheravakkattu G. Suresh、Jean-Luc Décout、Tanmaya Pathak

  DOI：10.1016/j.carres.2008.03.022

  日期：2008.6

  When 3-C-sulfonyl-pent-2-enofuranosides and 3-C-sulfonyl-hex-2-enofuranosides were reacted with primary and secondary amines, only the beta-anomeric methoxy group of the pent-2-enofuranoside did not cause any hindrance to incoming nitrogen nucleophiles. This resulted in the 'unusual' addition of amines, in which the diastereoselectivity of the reaction was overwhelmingly in favor of amino sugars of the D-arabino configuration. Selected products were desulfonylated to obtain a new class of beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides. (C) 2008 Elsevier Ltd. All rights reserved.