2,3-O-isopropylidene-D-xylose diethyl dithioacetal | 53872-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-D-xylose diethyl dithioacetal
• 英文别名: (1R)-1-[(4S,5R)-5-[bis(ethylsulfanyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 53872-69-8
• 化学式: C₁₂H₂₄O₄S₂
• 分子量: 296.452
• InChiKey: LPWNOTKGDBWAQD-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-D-xylose diethyl dithioacetal 在 lead(IV) acetate 作用下， 以 甲苯 为溶剂， 反应 0.33h， 生成 2,3-O-isopropylidene-L-threo-tetrodialdose 1,1-diethyl dithioacetal
  参考文献：
  名称：

  Efficient Synthesis of the Hexasaccharide Fragment of Landomycin A:  Using Phenyl 2,3-O-Thionocarbonyl-1-thioglycosides as 2-Deoxy-β-glycoside Precursors

  摘要：

  [GRAPHICS]The beta-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-Xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.

  DOI：

  10.1021/ol0259286
• 作为产物：
  描述：

  D-xylose diethyl dithioacetal 在 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 1.5h， 生成 2,3-O-isopropylidene-D-xylose diethyl dithioacetal
  参考文献：
  名称：

  Efficient Synthesis of the Hexasaccharide Fragment of Landomycin A:  Using Phenyl 2,3-O-Thionocarbonyl-1-thioglycosides as 2-Deoxy-β-glycoside Precursors

  摘要：

  [GRAPHICS]The beta-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-Xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.

  DOI：

  10.1021/ol0259286

文献信息

• The rearrangement of mono-O-isopropylidene derivatives of aldose diethyl dithioacetals
  作者：T. Bruce Grindley、Chandra Wickramage

  DOI：10.1016/0008-6215(87)80272-0

  日期：1987.9

  -Isopropylidene- d -mannose diethyl dithioacetal was also prepared directly from d -mannose diethyl dithioacetal. Consistent ratios of product to starting material indicated that the 4,5- trans -disubstituted 2,2-dimethyl-1,3-dioxolane products are ∼1.2 kcal.mol −1 more stable than the 4-substituted 2,2-dimethyl-1,3-dioxolane starting-materials. Reaction of d -glucose diethyl dithioacetal with an excess of 2-methoxypropene

  摘要研究了一些醛糖二乙基二硫缩醛在N，N-二甲基甲酰胺中的酸催化端基-O-异亚丙基衍生物的重排。d-阿拉伯糖和d-木糖二乙基二硫缩醛的4，5-O-异亚丙基衍生物分别重排至2，3-和2，3-和3，4-和3，4-O-异亚丙基衍生物的混合物。d-半乳糖，d-甘露糖和d-葡萄糖的5,6- O-异亚丙基衍生物重新排列为4,5、3,4-和2,3-和3,4-O的混合物-异亚丙基衍生物。通过交叉实验，并考虑到所得产物的结构和重排速率，这些重排显示为分子内。3，还可以直接从d-甘露糖二乙基二硫缩醛制备4-O-异亚丙基-d-甘露糖二乙基二硫缩醛。产物与起始物质的比例一致表明，4,5-反式-二取代的2,2-二甲基-1,3-二氧戊环产物比4-取代的2,2-二甲基-酯稳定约1.2 kcal.mol -1。 1,3-二氧戊环原料。在高浓度和低浓度酸的存在下，d-葡萄糖二乙基二硫缩醛与过量的2-甲氧基丙烯反应，主要得到2
• A highly efficient practical method for the synthesis of chiral polyhydroxy-(E,E)-1-chlorodienols and (E)-5-hydroxy enynes
  作者：J.S. Yadav、D.K. Barma、Dinah Dutta

  DOI：10.1016/s0040-4039(97)00907-6

  日期：1997.6

  An efficient protocol for the synthesis of chiral polyhydroxy-(E, E)-1-chlorodienols and (E)-5-hydroxy enynes from chiral 4,5-epoxy trans allyl chlorides and 4,5-O-isopropylidene allyl chlorides is described by using stoichiometric amount of LiNH2 or LDA in HMPA : THF (1 : 5) useful in the synthesis of biologically active natural products. (C) 1997 Elsevier Science Ltd.
• Efficient Synthesis of the Hexasaccharide Fragment of Landomycin A:  Using Phenyl 2,3-<i>O</i>-Thionocarbonyl-1-thioglycosides as 2-Deoxy-β-glycoside Precursors
  作者：Biao Yu、Ping Wang

  DOI：10.1021/ol0259286

  日期：2002.5.1

  [GRAPHICS]The beta-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-Xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.