(R)-3,5-O-benzylidene-6-deoxy-2-O-trifluoromethanesulfonyl-L-glucono-1,4-lactone | 322726-65-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (R)-3,5-O-benzylidene-6-deoxy-2-O-trifluoromethanesulfonyl-L-glucono-1,4-lactone
• 英文别名: [(2R,4S,4aS,7S,7aR)-4-methyl-6-oxo-2-phenyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-7-yl] trifluoromethanesulfonate
• CAS: 322726-65-8
• 化学式: C₁₄H₁₃F₃O₇S
• 分子量: 382.314
• InChiKey: DGLQTBRPYIBXEN-YUGVXFKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (R)-3,5-O-benzylidene-6-deoxy-2-O-trifluoromethanesulfonyl-L-glucono-1,4-lactone 在 甲醇 、 potassium carbonate 、 对甲苯磺酸 、 乙酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 146.3h， 生成 methyl 2,4-anhydro (S)-3,5-O-benzylidene-L-rhamnonate
  参考文献：
  名称：

  Two epimerisations in the formation of oxetanes from l-rhamnose: towards oxetane-containing peptidomimetics

  摘要：

  The methyl group in (R)-3,5-O-benzylidene-L-rhamnono-1,4-lactone 2, prepared from L-rhamnose 1 in 41% yield without need for chromatography, is axial and provides a good example of Mills' rule that the 'O-inside' conformations are, in general, more stable than alternative 'H-inside' conformations. The lactone 2 may be converted in two steps in an overall 57% yield to the rhamnono-oxetane 3, which should be useful in generating oxetane dipeptide isosteres and oxetane beta -amino acids and in determining the value of the oxetane ring in inducing secondary structure in small peptidomimetics. Methyl 2,4-anhydro-(S)-3,5-O-benzylidene-L-rhamnonate 11, in which both the phenyl and methyl groups are equatorial, is slightly more thermodynamically stable than 3, providing a rare exception to Mills' rule. X-ray crystal structures of 2 and 11 are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00360-8
• 作为产物：
  描述：

  L-rhamnopyranose 在 吡啶 、 水 、 溴 、 氧化汞红 、 barium carbonate 作用下， 以 四氢呋喃 、 丁酮 为溶剂， 反应 20.4h， 生成 (R)-3,5-O-benzylidene-6-deoxy-2-O-trifluoromethanesulfonyl-L-glucono-1,4-lactone
  参考文献：
  名称：

  Two epimerisations in the formation of oxetanes from l-rhamnose: towards oxetane-containing peptidomimetics

  摘要：

  The methyl group in (R)-3,5-O-benzylidene-L-rhamnono-1,4-lactone 2, prepared from L-rhamnose 1 in 41% yield without need for chromatography, is axial and provides a good example of Mills' rule that the 'O-inside' conformations are, in general, more stable than alternative 'H-inside' conformations. The lactone 2 may be converted in two steps in an overall 57% yield to the rhamnono-oxetane 3, which should be useful in generating oxetane dipeptide isosteres and oxetane beta -amino acids and in determining the value of the oxetane ring in inducing secondary structure in small peptidomimetics. Methyl 2,4-anhydro-(S)-3,5-O-benzylidene-L-rhamnonate 11, in which both the phenyl and methyl groups are equatorial, is slightly more thermodynamically stable than 3, providing a rare exception to Mills' rule. X-ray crystal structures of 2 and 11 are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00360-8

文献信息

• 6-Deoxyhexoses from<scp>l</scp>-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology
  作者：Zilei Liu、Akihide Yoshihara、Ciarán Kelly、John T. Heap、Mikkel H. S. Marqvorsen、Sarah F. Jenkinson、Mark R. Wormald、José M. Otero、Amalia Estévez、Atsushi Kato、George W. J. Fleet、Ramón J. Estévez、Ken Izumori

  DOI：10.1002/chem.201602482

  日期：2016.8.22

  In the search for alternative non‐metabolizable inducers in the l‐rhamnose promoter system, the synthesis of fifteen 6‐deoxyhexoses from l‐rhamnose demonstrates the value of synergy between biotechnology and chemistry. The readily available 2,3‐acetonide of rhamnonolactone allows inversion of configuration at C4 and/or C5 of rhamnose to give 6‐deoxy‐d‐allose, 6‐deoxy‐d‐gulose and 6‐deoxy‐l‐talose. Highly

  在寻求在替代方案中不可代谢的诱导升鼠李糖启动子系统，十五6-脱氧己糖从合成升鼠李糖演示生物技术和化学之间的协同作用的值。rhamnonolactone的容易获得的2,3-丙酮允许构型的反转在C4和/或鼠李糖的C5，得到6-脱氧d -allose，6-脱氧d -gulose和6-脱氧升-talose。高度结晶的3,5-亚苄基rhamnonolactone可以轻松访问升-quinovose（6-脱氧升葡萄糖），升带有C2叠氮基，氨基和乙酰氨基取代基的寡糖和鼠李糖类似物。鼠李的亲电氟化作用产生了2-脱氧-2-氟-1-鼠李糖和2-脱氧-2-氟-1-鼠李糖的混合物。生物技术使人们能够获得6-脱氧-l-果糖和1-脱氧-l-果糖。
• Two epimerisations in the formation of oxetanes from l-rhamnose: towards oxetane-containing peptidomimetics
  作者：Stephen W Johnson、Donald Angus、Claude Taillefumier、John H Jones、David J Watkin、Emma Floyd、J.Grant Buchanan、George W.J Fleet

  DOI：10.1016/s0957-4166(00)00360-8

  日期：2000.10

  The methyl group in (R)-3,5-O-benzylidene-L-rhamnono-1,4-lactone 2, prepared from L-rhamnose 1 in 41% yield without need for chromatography, is axial and provides a good example of Mills' rule that the 'O-inside' conformations are, in general, more stable than alternative 'H-inside' conformations. The lactone 2 may be converted in two steps in an overall 57% yield to the rhamnono-oxetane 3, which should be useful in generating oxetane dipeptide isosteres and oxetane beta -amino acids and in determining the value of the oxetane ring in inducing secondary structure in small peptidomimetics. Methyl 2,4-anhydro-(S)-3,5-O-benzylidene-L-rhamnonate 11, in which both the phenyl and methyl groups are equatorial, is slightly more thermodynamically stable than 3, providing a rare exception to Mills' rule. X-ray crystal structures of 2 and 11 are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.