2,3:4,5-di-O-isopropylidene-D-lyxose diethyldithioacetal | 159144-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3:4,5-di-O-isopropylidene-D-lyxose diethyldithioacetal
• 英文别名: (4S,5S)-4-[bis(ethylsulfanyl)methyl]-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane
• CAS: 159144-38-4
• 化学式: C₁₅H₂₈O₄S₂
• 分子量: 336.517
• InChiKey: AQOSDHFQHXQKBE-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3:4,5-di-O-isopropylidene-D-lyxose diethyldithioacetal 在 mercury(II) oxide 、 magnesium chloride 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以89.8%的产率得到(4S,4'R,5S)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolane)]-5-carbaldehyde
  参考文献：
  名称：

  一种光刻胶树脂单体及其合成方法

  摘要：

  本发明公开了一种光刻胶树脂单体，涉及光刻胶领域，其结构式如下所示：其中R1和R2分别独立的为氢、烷烃或者环烷烃；R3为氢或者甲基；n为1～8，m为1～10的整数。与其它类型的树脂单体共聚形成光刻胶树脂，能够增加了曝光区和非曝光区在碱性显影液中的溶解速度差，降低粗糙度，提高灵敏度和分辨率，有利于形成均一性良好的光刻图案，特别适用于正性光刻胶；还可以增加耐刻蚀性能；并且起始原料为天然提取的糖类，原料来源广泛，合成方法简单。

  公开号：

  CN112625022A
• 作为产物：
  描述：

  2-O-(t-butylsimethylsilyl)-3,4-O-isopropylidene-D-threose 在 lithium aluminium tetrahydride 、 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.5h， 生成 2,3:4,5-di-O-isopropylidene-D-lyxose diethyldithioacetal
  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

文献信息

• Chelation-Assisted Regioselective C−O Bond Cleavage Reactions of Acetals by Grignard Reagents. A General Procedure for the Regioselective Synthesis of Protected Polyols Having One Free Hydroxy Group
  作者：Wen-Lung Cheng、Yeng-Jeng Shaw、Sue-Min Yeh、Puthuparampil P. Kanakamma、Yu-Huey Chen、Chuo Chen、Jia-Cheng Shieu、Shaang-Jyh Yiin、Gene-Hsiang Lee、Yu Wang、Tien-Yau Luh

  DOI：10.1021/jo981579a

  日期：1999.1.1

  Acetals containing a neighboring heteroatom react with the Grignard reagent in aromatic hydrocarbon solvents regioselectively. The auxiliary moiety can be hydroxy, alkoxy, or amino but not sulfur. Chelation plays a key role in directing the regioselectivity of this ring opening reaction. The reactions of acetonide derivatives of monosaccharides under these conditions afford the corresponding products having only one free hydroxy group at the specific position. Fully protected mannosamine derivative is prepared in good yield. The stereochemistry of the carbon center where auxiliary group is attached can be either syn or anti to the acetal oxygen moiety where cleavage of the C-O bond occurs. However, difference in reactivity has been found in the reaction of tris-acetonide of sorbitol with MeMgI. Regioselective ring opening of the acetal group at the anomeric carbon generates a hemiacetal which underwent further nucleophilic addition to furnish the corresponding alcohol stereoselectively.
• Eine einfache Synthese aller vier stereoisomeren 2,2,5-Trimethyl-1,3-dioxolan-4-carbaldehyde
  作者：W. H. Binder、R. H. Prenner、W. Schmid

  DOI：10.1007/bf01277638

  日期：1994.6

  A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.
• Cheng Wen-Lung, Yeh Sue-Min, Luh Tien-Ya, J. Org. Chem, 58 (1993) N 21, S 5576-5577
  作者：Cheng Wen-Lung, Yeh Sue-Min, Luh Tien-Ya

  DOI：——

  日期：——
• 一种光刻胶树脂单体及其合成方法
  申请人：上海博栋化学科技有限公司

  公开号：CN112625022A

  公开（公告）日：2021-04-09

  本发明公开了一种光刻胶树脂单体，涉及光刻胶领域，其结构式如下所示：其中R1和R2分别独立的为氢、烷烃或者环烷烃；R3为氢或者甲基；n为1～8，m为1～10的整数。与其它类型的树脂单体共聚形成光刻胶树脂，能够增加了曝光区和非曝光区在碱性显影液中的溶解速度差，降低粗糙度，提高灵敏度和分辨率，有利于形成均一性良好的光刻图案，特别适用于正性光刻胶；还可以增加耐刻蚀性能；并且起始原料为天然提取的糖类，原料来源广泛，合成方法简单。
• 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.