(4R,5R)-<5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-yl>methyl p-toluenesulfonate | 73711-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,5R)-<5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-yl>methyl p-toluenesulfonate
• 英文别名: (4R,5R)-<5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl>methyl p-toluenesulfonate；(2R,3R)-2,3-(propane-2,2-dioxy)-4-hydroxy-1-butyl p-toluenesulfonate；(2S,3S)-2,3-Isopropylidenedioxy-4-tosyloxybutan-1-ol；2,3-O-isopropylidene-1-O-tosyl-D-threitol；(4R,5R)-[5-Hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-methyl P-toluenesulfonate；(4R,5R)-[5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl p-toluenesulfonate；((4R,5R)-5-(hydroxyMethyl)-2,2-diMethyl-1,3-dioxolan-4-yl)Methyl 4-Methylbenzenesulfonate；[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 73711-65-6
• 化学式: C₁₄H₂₀O₆S
• 分子量: 316.375
• InChiKey: OKTMEOCGDWUZIU-CHWSQXEVSA-N

物化性质

• 沸点：
  457.6±25.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R)-<5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-yl>methyl p-toluenesulfonate 在 lithium aluminium tetrahydride 、 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde
  参考文献：
  名称：

  Versicolactones A and B: total synthesis and structure revision

  摘要：

  To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The H-1 and C-13 NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta-2,4-dien-4-lactone, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.120
• 作为产物：
  描述：

  (4R,5R)-4,5-二乙氧基羰基-2,2-二甲基二氧 在 吡啶 、 lithium aluminium tetrahydride 作用下， 生成 (4R,5R)-<5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-yl>methyl p-toluenesulfonate
  参考文献：
  名称：

  Fujimoto, Yasuo; Satoh, Mitsuru; Takeuchi, Naoki, Chemistry Letters, 1989, p. 1619 - 1622

  摘要：

  DOI：

文献信息

• Formation of sulfinate esters in the synthesis of triflates
  作者：Thomas Netscher、Patrick Bohrer

  DOI：10.1016/0040-4039(96)01930-2

  日期：1996.11

  and phenols with triflic anhydride in the presence of amines, trifluoromethanesulfinyl esters were unexpectedly found. Depending on the reaction conditions and the structures of both hydroxy compound and base, esterified products (yields <5% to 99%) containing 0% to 89% (!) of sulfinates were obtained. The mechanisms of these reactions are discussed. The results of the present study indicate how to

  在胺的存在下用三氟甲磺酸酐对空间拥挤的醇和苯酚进行标准处理时，出乎意料地发现了三氟甲亚磺酰基酯。根据反应条件以及羟基化合物和碱的结构，获得了包含0-89％（1）的亚磺酸盐的酯化产物（产率＜5％至99％）。讨论了这些反应的机理。本研究的结果表明如何避免在三氟甲磺酸酯合成中形成不必要的亚磺酸盐。
• Synthesis of stereochemical probes for new fluorogenic assays for yeast transketolase variants
  作者：Aurélie Sevestre、Franck Charmantray、Virgil Hélaine、Angelika Lásiková、Laurence Hecquet

  DOI：10.1016/j.tet.2006.02.033

  日期：2006.4

  For the screening of yeast transketolase (TK) variants with improved or new properties acquired by random mutagenesis, we report on the stereoselective synthesis of fluorogenic substrates as probes for measuring TK activity. Compound 1 (7-(2′,3′,5′-trihydroxy-4′-oxo-pentyl)oxycoumarine), prepared as previously described, [Tetrahedron Lett.2003, 44, 827–830] enabled us to evaluate wild type TK velocity

  为了筛选通过随机诱变获得的具有改进或新特性的酵母转酮醇酶（TK）变体，我们报道了荧光底物的立体选择性合成，作为测量TK活性的探针。如前所述，制备的化合物1（7-（2'，3'，5'-三羟基-4'-氧代戊基）氧基香豆素）[ Tetrahedron Lett。2003，44，827-830]让我们在一个简单的，具体的和可重复的方法来评估野生型TK速度。为了选择能够产生D-苏糖醛糖的TK突变体，我们从酒石酸二甲酯制备了化合物2（二羟基-4-O-（（2'-氧代-苯并吡喃-7'-基-D-苏糖））。我们成功地获得了化合物3（7'-（2,3,5-三羟基-4-氧代戊基）氧基香豆素）作为能够产生异赤酮酮糖的TK突变体的探针。
• Total Synthesis of (−)-Agelastatin A: The Application of a Sequential Sigmatropic Rearrangement
  作者：Naoto Hama、Tomoki Matsuda、Takaaki Sato、Noritaka Chida

  DOI：10.1021/ol900799e

  日期：2009.6.18

  An enantioselective total synthesis of (−)-agelastatin A from (−)-2,3-O-isopropylidene-d-threitol is described. The sequential Overman/Mislow−Evans rearrangement of the allylic bistrichloroimidate is the key step, which efficiently installed a diaminohydroxy group.

  的对映体选择性全合成（ - ） - agelastatin甲从（ - ） - 2,3- Ô异亚丙基d -threitol进行说明。烯丙基双三氯亚氨酸酯的连续Overman / Mislow-Evans重排是关键步骤，该步骤有效地安装了二氨基羟基。
• Synthesis and absolute configurations of the cytotoxic polyacetylenes isolated from the callus of Panax ginseng.
  作者：Yasuo FUJIMOTO、Mitsuru SATOH、Naoki TAKEUCHI、Makoto KIRISAWA

  DOI：10.1248/cpb.38.1447

  日期：——

  Panaxacol (1) and dihydropanaxacol (2), cytotoxic polyacetylenes isolated from the callus of Panax ginseng, were synthesized starting from D-(-)-diethyl tartrate. The absolute configuration of 1 was determined to be 9R, 10R and the absolute configuration at C-3 of 2 was tentatively assigned as 3S by the application of the R(+)-alpha-methoxy-alpha-(trifluoro methyl)phenylacetyl (MTPA) method.

  从人参愈伤组织中分离出的具有细胞毒性的聚乙炔，人参醇（1）和二氢人参醇（2）从酒石酸D-（-）-二乙酯开始合成。通过应用R（+）-α-甲氧基-α-（三氟甲基）苯乙酰基（MTPA），确定1的绝对构型为9R，10R，并将C-3为2的绝对构型暂定为3S。 ） 方法。
• Mixtures and compositions suitable for controlling Hylotrupes bajulus and Pyrrhidium sanguineum
  申请人：BASF Aktiengesellschaft

  公开号：US06245328B1

  公开（公告）日：2001-06-12

  A mixture containing one stereoisomer of 3-hydroxyhexan-2-one and two stereoisomers of hexane-2,3-diol, especially (3R)-3-hydroxy-hexan-2-one, (2R,3R)-hexane-2,3-diol and/or (2R,3R)-hexane-2,3-diol and compositions containing them and the use of the mixture and of the compositions for controlling Hylotrupes bajulus and Pyrrhidium sanguineum by means of the monitoring, capture or mating disruption method are described.

  一种含有3-羟基己酮的立体异构体和两种己二醇的立体异构体的混合物，特别是(3R)-3-羟基己酮，(2R,3R)-己二醇和/或(2R,3R)-己二醇，以及含有它们的组合物，以及利用该混合物和组合物通过监测、捕获或交配干扰方法控制松墨天牛和血红松天牛的用途已经被描述。