methyl 5,6-O-cyclohexylidene-2,3-dideoxy-3-C-(p-tolylsulfonyl)-α-D-erythro-hex-2-enofuranoside | 884500-00-9

• 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 5,6-O-cyclohexylidene-2,3-dideoxy-3-C-(p-tolylsulfonyl)-α-D-erythro-hex-2-enofuranoside
• 英文别名: (3R)-3-[(2R,5S)-5-methoxy-3-(4-methylphenyl)sulfonyl-2,5-dihydrofuran-2-yl]-1,4-dioxaspiro[4.5]decane
• CAS: 884500-00-9
• 化学式: C₂₀H₂₆O₆S
• 分子量: 394.489
• InChiKey: KPDLJRRUKLOMMJ-NZSAHSFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5,6-O-cyclohexylidene-2,3-dideoxy-3-C-(p-tolylsulfonyl)-α-D-erythro-hex-2-enofuranoside 在 magnesium 、 nickel dibromide 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 methyl 5,6-O-cyclohexylidene-2,3-dideoxy-2-morpholino-α-D-altrofuranoside
  参考文献：
  名称：

  Desulfonylation with Mg−MeOH−NiBr₂:  An Expedient Reagent System for the Synthesis of 2-Amino-2,3-dideoxy Furanosides

  摘要：

  A catalytic amount of NiBr2 with Mg-MeOH increases the efficiency of reductive desulfonylation of the beta-sulfonylated aminosugars. The Mg-MeOH-NiBr2 system has been utilized in the synthesis of 2-amino-2,3-dideoxypentofuranosides and 2-amino-2,3-dideoxyhexofuranosides. The yield of the desulfonylation improved dramatically from 0% with the known reagents to 44-75% with Mg-MeOH-NiBr2.

  DOI：

  10.1021/ol053082a
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以0.94 g的产率得到methyl 5,6-O-cyclohexylidene-2,3-dideoxy-3-C-(p-tolylsulfonyl)-α-D-erythro-hex-2-enofuranoside
  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

• Densely Functionalized Chiral Pyrroles from Endocyclic, Exocyclic, and Acyclic Vinyl Sulfone-Modified Carbohydrates
  作者：Rahul Bhattacharya、Ananta Kumar Atta、Debanjana Dey、Tanmaya Pathak

  DOI：10.1021/jo801948m

  日期：2009.1.16

  A wide range of vinyl sulfone-modified carbohydrates have been prepared as starting materials for the synthesis of polysubstituted chiral pyrroles. All these vinyl sulfones reacted efficiently with ethylisocyanoacetate to generate a plethora of new pyrrole derivatives. Furanosyl rings opened up during pyrrole synthesis, and pyranosyl rings were opened up by reacting the pyrrole with POCl3/DMF. This paper also reports one of the most efficient and practical routes for the synthesis of beta-substituted pyrroles.