2,3-O-isopropylidene-2-C-methyl-5-O-trifluoromethanesulfonyl-D-lyxono-1,4-lactone | 926659-27-0

• 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: 2,3-O-isopropylidene-2-C-methyl-5-O-trifluoromethanesulfonyl-D-lyxono-1,4-lactone
• 英文别名: [(3aS,6R,6aS)-2,2,3a-trimethyl-4-oxo-6,6a-dihydrofuro[3,4-d][1,3]dioxol-6-yl]methyl trifluoromethanesulfonate
• CAS: 926659-27-0
• 化学式: C₁₀H₁₃F₃O₇S
• 分子量: 334.27
• InChiKey: BSZHXUSSDKQRAC-JHEQGTHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  2,3-O-isopropylidene-2-C-methyl-5-O-trifluoromethanesulfonyl-D-lyxono-1,4-lactone 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以82%的产率得到2,3-O-(1-methylethylidene)-2-C-methyl-L-ribono-1,4-lactone
  参考文献：
  名称：

  Green aldose isomerisation: 2-C-methyl-1,4-lactones from the reaction of Amadori ketoses with calcium hydroxide

  摘要：

  Saccharinic acids, branched 2-C-methyl-aldonic acids, may be accessed via a green procedure from aldoses by sequential conversion to an Amadori ketose and treatment with calcium hydroxide; D-galactose and D-glucose are converted to 2-C-methyl-D-lyxono-1,4-lactone (with a small amount of 2-C-methyl-D-xylono-1,4-lactone) and 2-C-methyl-D-ribono-1,4-lactone. Inversion of configuration at C-4 of the branched lactones allows access to 2-C-methyl-L-ribono-1,4-lactone and 2-C-methyl-L-lyxono-1,4-lactone, respectively. D-Xylose affords 2-C-methyl-D-threono-1,4-lactone and 2-C-methyl-D-erythrono-1,4-lactone, whereas L-arabinose, under similar conditions, gave the enantioiners 2-C-methyl-L-lactone-1,4-lactone and 2-C-methyl-L-erythrono-1,4-lactone. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2006.11.137
• 作为产物：
  描述：

  (2R,3S,4S,5R)-2-[(dibenzylamino)methyl]oxane-2,3,4,5-tetrol 在 吡啶 、 copper(II) sulfate 、 calcium oxide 作用下， 以 二氯甲烷 、 硫酸 、 水 为溶剂， 反应 24.0h， 生成 2,3-O-isopropylidene-2-C-methyl-5-O-trifluoromethanesulfonyl-D-lyxono-1,4-lactone
  参考文献：
  名称：

  Green aldose isomerisation: 2-C-methyl-1,4-lactones from the reaction of Amadori ketoses with calcium hydroxide

  摘要：

  Saccharinic acids, branched 2-C-methyl-aldonic acids, may be accessed via a green procedure from aldoses by sequential conversion to an Amadori ketose and treatment with calcium hydroxide; D-galactose and D-glucose are converted to 2-C-methyl-D-lyxono-1,4-lactone (with a small amount of 2-C-methyl-D-xylono-1,4-lactone) and 2-C-methyl-D-ribono-1,4-lactone. Inversion of configuration at C-4 of the branched lactones allows access to 2-C-methyl-L-ribono-1,4-lactone and 2-C-methyl-L-lyxono-1,4-lactone, respectively. D-Xylose affords 2-C-methyl-D-threono-1,4-lactone and 2-C-methyl-D-erythrono-1,4-lactone, whereas L-arabinose, under similar conditions, gave the enantioiners 2-C-methyl-L-lactone-1,4-lactone and 2-C-methyl-L-erythrono-1,4-lactone. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2006.11.137

文献信息

• Homochiral carbon branched piperidines from carbon branched sugar lactones: 4-C-methyl-deoxyfuconojirimycin (DFJ) and its enantiomer—removal of glycosidase inhibition
  作者：David J. Hotchkiss、Atsushi Kato、Barbara Odell、Timothy D.W. Claridge、George W.J. Fleet

  DOI：10.1016/j.tetasy.2007.02.001

  日期：2007.3

  The value of readily available 2-C-methyl aldonic acids in short syntheses of carbon branched piperidines containing quaternary centers is demonstrated. The effect of the introduction of a 4-C-methyl group into piperidine imino sugar inhibitors of L-fucosidases and D-galactosidases is reported. (c) 2007 Elsevier Ltd. All rights reserved.
• Green aldose isomerisation: 2-C-methyl-1,4-lactones from the reaction of Amadori ketoses with calcium hydroxide
  作者：David J. Hotchkiss、Raquel Soengas、Kathrine V. Booth、Alexander C. Weymouth-Wilson、Vanessa Eastwick-Field、George W.J. Fleet

  DOI：10.1016/j.tetlet.2006.11.137

  日期：2007.1

  Saccharinic acids, branched 2-C-methyl-aldonic acids, may be accessed via a green procedure from aldoses by sequential conversion to an Amadori ketose and treatment with calcium hydroxide; D-galactose and D-glucose are converted to 2-C-methyl-D-lyxono-1,4-lactone (with a small amount of 2-C-methyl-D-xylono-1,4-lactone) and 2-C-methyl-D-ribono-1,4-lactone. Inversion of configuration at C-4 of the branched lactones allows access to 2-C-methyl-L-ribono-1,4-lactone and 2-C-methyl-L-lyxono-1,4-lactone, respectively. D-Xylose affords 2-C-methyl-D-threono-1,4-lactone and 2-C-methyl-D-erythrono-1,4-lactone, whereas L-arabinose, under similar conditions, gave the enantioiners 2-C-methyl-L-lactone-1,4-lactone and 2-C-methyl-L-erythrono-1,4-lactone. (c) 2006 Published by Elsevier Ltd.