benzyl 2,3-O-(1-methylethylidene)-α-L-lyxofuranosiduronaldehyde | 583829-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3-O-(1-methylethylidene)-α-L-lyxofuranosiduronaldehyde
• 英文别名: benzyl 2,3-O-isopropylidene-D-riboside-6-aldehyde；benzyl (5R)-3,4-O-(1-methylethylidene)-L-arabino-pentodialdo-5,2-furanoside；(3aR,4R,6R,6aR)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carbaldehyde
• CAS: 583829-31-6
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: OGBMDKPBMYYRMN-REWJHTLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-O-(1-methylethylidene)-α-L-lyxofuranosiduronaldehyde 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 silver nitrate 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 20.0h， 生成 2,3-O-(1-methylethylidene)-5,5-di-C-phenyl-α-L-lyxofuranose
  参考文献：
  名称：

  D-古洛内酯作为L-新葡聚糖的合成子：首先制备4-O-去甲基-L-新呋喃糖及相关衍生物。

  摘要：

  [反应：见正文]提出了新生物素的糖部分L-新葡聚糖（11）的新合成方法。D-古洛内酯最初在几个步骤中转化为关键酯衍生物7 [1-O-苄基甲基2,3-O-（1-甲基乙叉基）-α-L-呋喃呋喃二糖醛酸酯]。适当地选择保护基使得在温和的反应条件下7可以转化为4-O-脱甲基-L-新呋喃糖9a和相关的9b-c。衍生物9进一步转化为L-lyxopyranoses（10a和10b）或甲基L-lyx呋喃糖苷12。

  DOI：

  10.1021/ol034796t
• 作为产物：
  描述：

  D-(-)-古洛糖酸-gamma-内酯 在 硫酸 、 SiO₂-supported NaIO₄ 、 四丁基碘化铵 、 二异丁基氢化铝 、 copper(II) sulfate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl 2,3-O-(1-methylethylidene)-α-L-lyxofuranosiduronaldehyde
  参考文献：
  名称：

  1-C-Alkyl imino-d-xylitol and -l-arabinitol derivatives obtained via nucleophilic addition to pentose-derived N-tert-butanesulfinyl imines: sugar- versus chiral auxiliary-induced stereoselectivity

  摘要：

  The stereoselective synthesis of 1-C-alkyl iminosugars in the D-xylo and L-arabino series as potential drugs for the treatment of lysosomal diseases has been achieved. The key step involves nucleophilic addition to pentodialdofuranose-derived imines generated using enantiopure tert-butanesulfinamide. Depending on the pentofuranose configuration and structure, the stereoselectivity of this reaction was found to be controlled either by the sugar moiety or by the stereogenic sulfur center. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.024

文献信息

• FeIII-Catalyzed Synthesis of Primary Amides from Aldehydes
  作者：Ravikumar R. Gowda、Debashis Chakraborty

  DOI：10.1002/ejoc.201001738

  日期：2011.4

  A direct synthetic route for the transformation of aldehydes into primary amides in the presence of catalytic amounts of FeCl 3 in water is described.

  描述了在水中催化量的 FeCl 3 存在下将醛转化为伯酰胺的直接合成路线。
• Highly Diastereoselective Synthesis of <i>C</i>-Glycosides from Glycal Anomers
  作者：Lisi Yuan、Ya Fang、Zhaobo Zhou、Tinghong Lv、Yingpeng Su、Jian Liu、Xiaolei Wang

  DOI：10.1021/acs.orglett.3c01605

  日期：2023.6.16

  This Letter presents a highly diastereoselective synthesis of C-hydroxymethine glycosides from glycal anomers using a chiral N-heterocyclic carbene–copper catalyst. The high diastereoselectivity was synergistically controlled by the stereocenter of the substrate and chirality of the N-heterocyclic carbene–copper complex without being interrupted by the stereochemistry of C5 and the anomeric position

  这封信介绍了使用手性N -杂环卡宾 - 铜催化剂从甘醇异头物高度非对映选择性合成C -羟基次甲基糖苷。高非对映选择性受底物的立体中心和N-杂环卡宾-铜配合物的手性协同控制，而不会被 C5 的立体化学和端基异构位置打断。这种方法能够使用合成通用的糖醛和各种功能化的醛来生产各种C-羟基次甲基糖苷。
• 1-C-Alkyl imino-d-xylitol and -l-arabinitol derivatives obtained via nucleophilic addition to pentose-derived N-tert-butanesulfinyl imines: sugar- versus chiral auxiliary-induced stereoselectivity
  作者：Farah Oulaïdi、Estelle Gallienne、Philippe Compain、Olivier R. Martin

  DOI：10.1016/j.tetasy.2011.02.024

  日期：2011.3

  The stereoselective synthesis of 1-C-alkyl iminosugars in the D-xylo and L-arabino series as potential drugs for the treatment of lysosomal diseases has been achieved. The key step involves nucleophilic addition to pentodialdofuranose-derived imines generated using enantiopure tert-butanesulfinamide. Depending on the pentofuranose configuration and structure, the stereoselectivity of this reaction was found to be controlled either by the sugar moiety or by the stereogenic sulfur center. (C) 2011 Elsevier Ltd. All rights reserved.
• <scp>d</scp>-Gulonolactone as a Synthon for <scp>l</scp>-Noviose:  First Preparation of 4-<i>O</i>-Demethyl-<scp>l</scp>-noviofuranose and Related Derivatives
  作者：Marjan Ješelnik、Ivan Leban、Slovenko Polanc、Marijan Kočevar

  DOI：10.1021/ol034796t

  日期：2003.7.1

  D-Gulonolactone was initially converted in a few steps to the key ester derivative 7 [1-O-benzyl methyl 2,3-O-(1-methylethylidene)-alpha-L-lyxofuranosiduronate]. An appropriate selection of protecting groups enabled transformation of 7 under mild reaction conditions to 4-O-demethyl-L-noviofuranose 9a and related 9b-c. Derivatives 9 were further converted either to L-lyxopyranoses (10a and 10b) or to

  [反应：见正文]提出了新生物素的糖部分L-新葡聚糖（11）的新合成方法。D-古洛内酯最初在几个步骤中转化为关键酯衍生物7 [1-O-苄基甲基2,3-O-（1-甲基乙叉基）-α-L-呋喃呋喃二糖醛酸酯]。适当地选择保护基使得在温和的反应条件下7可以转化为4-O-脱甲基-L-新呋喃糖9a和相关的9b-c。衍生物9进一步转化为L-lyxopyranoses（10a和10b）或甲基L-lyx呋喃糖苷12。