S-phenyl 3,4-di-O-benzyl-2-O-cyano-1-thio-β-L-rhamnopyranoside | 848397-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-phenyl 3,4-di-O-benzyl-2-O-cyano-1-thio-β-L-rhamnopyranoside
• 英文别名: [(2R,3R,4R,5S,6S)-6-methyl-4,5-bis(phenylmethoxy)-2-phenylsulfanyloxan-3-yl] cyanate
• CAS: 848397-92-2
• 化学式: C₂₇H₂₇NO₄S
• 分子量: 461.582
• InChiKey: NOJNSJFAJCPPTH-CMKGNXEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-phenyl 3,4-di-O-benzyl-2-O-cyano-1-thio-β-L-rhamnopyranoside 、 双丙酮葡萄糖 在 2,4,6-三甲基嘧啶 、 1-(苯基亚硫酰基)哌啶 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以21%的产率得到3-O-(3,4-di-O-benzyl-2-O-cyano-α-L-rhamnopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Disarming, non-participating 2-O-protecting groups in manno- and rhamnopyranosylation: scope and limitations of sulfonates, vinylogous esters, phosphates, cyanates, and nitrates

  摘要：

  A series of D-mannopyranosyl and L-rhamnopyranosyl thioglycosides; protected with electron-withdrawing non-participating protecting groups on O-2 have been prepared and investigated for their potential as beta-glycosyl donors. Both alpha- and beta-thioglycosides were investigated and the latter preferred on the grounds of enhanced stability at room temperature. A 2-O-nitro-L-rhamnosyl fluoride was also prepared and investigated. Moderate beta-selectivities were observed with some of these donors. With the more powerfully electron-withdrawing groups reduced donor reactivity leads to a requirement for higher reaction temperatures and reduced selectivities. Decomposition temperatures of the intermediate glycosyl triflates were determined by variable temperature NMR spectroscopy and generally correlate with the disarming propensity of the protecting group system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.032
• 作为产物：
  描述：

  S-phenyl 3,4-di-O-benzyl-1-thio-β-L-rhamnopyranoside 在 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 S-phenyl 3,4-di-O-benzyl-2-O-cyano-1-thio-β-L-rhamnopyranoside
  参考文献：
  名称：

  Disarming, non-participating 2-O-protecting groups in manno- and rhamnopyranosylation: scope and limitations of sulfonates, vinylogous esters, phosphates, cyanates, and nitrates

  摘要：

  A series of D-mannopyranosyl and L-rhamnopyranosyl thioglycosides; protected with electron-withdrawing non-participating protecting groups on O-2 have been prepared and investigated for their potential as beta-glycosyl donors. Both alpha- and beta-thioglycosides were investigated and the latter preferred on the grounds of enhanced stability at room temperature. A 2-O-nitro-L-rhamnosyl fluoride was also prepared and investigated. Moderate beta-selectivities were observed with some of these donors. With the more powerfully electron-withdrawing groups reduced donor reactivity leads to a requirement for higher reaction temperatures and reduced selectivities. Decomposition temperatures of the intermediate glycosyl triflates were determined by variable temperature NMR spectroscopy and generally correlate with the disarming propensity of the protecting group system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.032