3,4-O-Isopropylidene-D-erythrose diethyl dithioacetal | 111205-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-O-Isopropylidene-D-erythrose diethyl dithioacetal
• 英文别名: 3,4-O-isopropylidene-D-erythrose diethyldithioacetal；(1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-bis(ethylsulfanyl)ethanol
• CAS: 111205-94-8
• 化学式: C₁₁H₂₂O₃S₂
• 分子量: 266.426
• InChiKey: MVOUOWKNSPPBOS-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  89.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-O-Isopropylidene-D-erythrose diethyl dithioacetal 在 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 水 、 对甲苯磺酸 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 56.5h， 生成 2,3:4,5-di-O-isopropylidene-D-ribose diethyl dithioacetal
  参考文献：
  名称：

  Stereoselective preparation of O-alkoxy d-tetrose, d-pentose, 2-deoxy-d-glycero tetrose and 2,3-dideoxy-d-erythro pentose derivatives by an iterative elongation of 2,3-O-isopropylidene-d-glyceraldehyde

  摘要：

  All D-pentoses are synthesized by one-carbon chain elongation commencing with the addition of the lithium salt of ethyl ethylthiomethyl sulfoxide to 2-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-D-erythrose and D-threose, 16 and 17. The addition of the above-mentioned nucleophile to 2-deoxy-3,4-O-isopropylidene-D-glycero tetrose, 19, gave rise to 2,3-dideoxy-D-glycero pentose. The starting aldehydes, 16, 17 and 19, are easily available from 2,3-O-isopropylidene-D-glyceraldehyde, 1, and ethyl ethylthiomethyl sulfoxide. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00072-5
• 作为产物：
  描述：

  (R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-ethanesulfinyl-2-ethylsulfanyl-ethanol 在 碘 、 三(二甲胺基)膦 作用下， 以 乙腈 为溶剂， 以40%的产率得到3,4-O-Isopropylidene-D-erythrose diethyl dithioacetal
  参考文献：
  名称：

  Analysis of the reactivity of the dithioacetal mono-S-oxide 1-deoxy-1-ethylsulfinyl-1-ethylthio-3,4-O-isopropylidene-D-erythritol under different conditions of reduction

  摘要：

  The chemistry of dithioacetal mono-S-oxides has not been studied very frequently. Their usual chemistry aims at recovering the carbonyl function by a sequence of reduction and hydrolysis. The results of the transformation of the dithioacetal mono-S-oxides of 1-deoxy-1-ethylsulfinyl-1-ethylthio-3,4-O-isopropylidene-D-erythritol, 2, under different reduction conditions, are reported in this paper. We also report how the coexistence of functional groups influences the resulting products. Hence, reductions with LiAlH4, Ph(3)P, (Me(2)N)(3)P, (CF3CO)(2)O-NaI and AcONa-Ac2O under Pummerer-type rearrangements have been studied.

  DOI：

  10.1039/p19960002933

文献信息

• Gonzales, D. Galisteo; Sastre, J. A. Lopez; Garcia, H. Martinez, Anales de Quimica, 1994, vol. 90, # 2, p. 212 - 216
  作者：Gonzales, D. Galisteo、Sastre, J. A. Lopez、Garcia, H. Martinez、Amo, J. F. Rodriguez、Tejedor, M. A. Sanz

  DOI：——

  日期：——
• Stereoselective preparation of O-alkoxy d-tetrose, d-pentose, 2-deoxy-d-glycero tetrose and 2,3-dideoxy-d-erythro pentose derivatives by an iterative elongation of 2,3-O-isopropylidene-d-glyceraldehyde
  作者：Y Arroyo-Gómez、J.A López-Sastre、J.F Rodrı́guez-Amo、M Santos-Garcı́a、M.A Sanz-Tejedor

  DOI：10.1016/s0957-4166(99)00072-5

  日期：1999.3

  All D-pentoses are synthesized by one-carbon chain elongation commencing with the addition of the lithium salt of ethyl ethylthiomethyl sulfoxide to 2-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-D-erythrose and D-threose, 16 and 17. The addition of the above-mentioned nucleophile to 2-deoxy-3,4-O-isopropylidene-D-glycero tetrose, 19, gave rise to 2,3-dideoxy-D-glycero pentose. The starting aldehydes, 16, 17 and 19, are easily available from 2,3-O-isopropylidene-D-glyceraldehyde, 1, and ethyl ethylthiomethyl sulfoxide. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Analysis of the reactivity of the dithioacetal mono-S-oxide 1-deoxy-1-ethylsulfinyl-1-ethylthio-3,4-O-isopropylidene-<scp>D</scp>-erythritol under different conditions of reduction
  作者：Yolanda Arroyo-Gómez、Juan A. López-Sastre、J. Felix Rodríguez-Amo、Ma Ascension Sanz-Tejedor

  DOI：10.1039/p19960002933

  日期：——

  The chemistry of dithioacetal mono-S-oxides has not been studied very frequently. Their usual chemistry aims at recovering the carbonyl function by a sequence of reduction and hydrolysis. The results of the transformation of the dithioacetal mono-S-oxides of 1-deoxy-1-ethylsulfinyl-1-ethylthio-3,4-O-isopropylidene-D-erythritol, 2, under different reduction conditions, are reported in this paper. We also report how the coexistence of functional groups influences the resulting products. Hence, reductions with LiAlH4, Ph(3)P, (Me(2)N)(3)P, (CF3CO)(2)O-NaI and AcONa-Ac2O under Pummerer-type rearrangements have been studied.