β-D-galactopyranosyl cyanide | 3737-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl cyanide
• 英文别名: beta-Galactopyranosyl cyanide；(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-carbonitrile
• CAS: 3737-59-5
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: NNWGBANFKDPMSI-MLKOFDEISA-N

物化性质

• 熔点：
  115-116 °C(Solv: isopropanol (67-63-0))
• 沸点：
  492.6±45.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  β-D-galactopyranosyl cyanide 在 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 (9H-fluoren-9-yl)methyl (((2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)methyl)carbamate
  参考文献：
  名称：

  WO2024077006A1

  摘要：

  公开号：
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 4.0h， 生成 β-D-galactopyranosyl cyanide
  参考文献：
  名称：

  （-）-Daucic acid：构型，合成和生物合成含义的修订。

  摘要：

  DOI：

  10.1002/anie.200352718

文献信息

• Pd-catalyzed coupling reactions of anhydro-aldose tosylhydrazones with aryl bromides to produce substituted exo -glycals
  作者：Tímea Kaszás、Anton Ivanov、Marietta Tóth、Peter Ehlers、Peter Langer、László Somsák

  DOI：10.1016/j.carres.2018.02.010

  日期：2018.8

  Palladium-catalyzed cross-couplings of O-peracylated and O-permethylated 2,6-anhydro-aldose tosylhydrazones with aryl halides were studied under thermic conditions in the presence of LiOtBu and phosphine ligands. The reactions gave the corresponding aryl substituted exo-glycals as mixtures of diastereomers in 11-75% yields. The transformations represent a new access to these types of glycomimetic compounds

  在LiOtBu和膦配体的存在下，在热条件下研究了钯催化的O-过酰基化和O-过甲基化的2,6-脱水醛糖甲苯磺酰with与芳基卤化物的交叉偶联。反应以11-75％的收率得到了相应的芳基取代的外二糖作为非对映异构体的混合物。转化代表了对这些类型的拟糖化合物的新途径。一些芳基取代的外糖基的双键被饱和，以得到良好的苄基C-糖基衍生物的产率。
• Synthesis of diazomethyl β-d-galactopyranosyl and β-d-glucopyranosyl ketones. Potential affinity-labeling reagents for carbohydrate-binding proteins
  作者：Robert Walter Myers、Yuan Chuan Lee

  DOI：10.1016/s0008-6215(00)90295-7

  日期：1986.9

  functional groups as their "aglycon", will be useful as enzyme-activated irreversible inhibitors (suicide substrates) of glycosidases, and as photoaffinity-labeling reagents and classical affinity-labeling reagents for carbohydrate-binding proteins.

  3,7-脱水-1-脱氧-1-重氮-D-甘油-L-甘露糖-2-辛糖（6a;重氮甲基β-D-吡喃半乳糖基酮）和3,7-脱水-1-脱氧-1-重氮已经制备了-D-甘油-D-gulo-2-辛糖（6b；重氮甲基β-D-吡喃葡萄糖基酮）。具有适当的立体化学和羟基保护作用的易得的C-糖基化合物，即过-O-乙酰基-2,6-脱水庚腈和过-O-乙酰基-2,6-脱水庚基酰胺，被用作前体。过-O-乙酰基-2,6-脱水庚酸。然后将这些关键中间体转化为混合的羧酸-碳酸酐，并使它们与重氮甲烷反应，得到相应的过-O-乙酰基-3,7-脱水-1-脱氧-1-重氮-2-辛糖。Zemplen脱乙酰化立体定向地以良好的总收率得到了结晶靶分子。
• Coupling Reactions of Anhydro-Aldose Tosylhydrazones with Boronic Acids
  作者：Tímea Kaszás、Balázs Áron Baráth、Bernadett Balázs、Tekla Blága、László Juhász、László Somsák、Marietta Tóth

  DOI：10.3390/molecules27061795

  日期：——

  A catalyst-free coupling reaction between O-peracetylated, O-perbenzoylated, O-permethylated, and O-permethoxymethylated 2,6-anhydro-aldose tosylhydrazones (C-(β-d-glycopyranosyl)formaldehyde tosylhydrazones) and aromatic boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope. The main products in most of the transformations were open-chain

  报道了 O-过乙酰化、O-过苯甲酰化、O-过甲基化和 O-过甲氧基甲基化 2,6-脱水-醛糖甲苯磺酰基腙（C-(β-d-吡喃糖基)甲醛甲苯磺酰基腙）与芳香硼酸之间的无催化剂偶联反应. 碱促进反应操作简单，底物范围广。大多数转化的主要产物是开链 1-C-芳基-hept-1-烯醇型化合物，而预期的 β-d-吡喃糖基甲基芳烃（苄基 C-糖苷）仅以次要产率形成。提供了一个机械原理来解释复杂的底物如何改变公认的反应过程。
• Preparation of 2-amino-2-C-glycosyl-acetonitriles from C-glycosyl aldehydes by Strecker reaction
  作者：Szabolcs Sipos、István Jablonkai、Orsolya Egyed、Mátyás Czugler

  DOI：10.1016/j.carres.2011.10.023

  日期：2011.12

  Synthesis of new 2-amino-2-C-D-glycosyl-acetonitriles in a Strecker reaction from various C-glycosyl aldehydes, chiral amines, and HCN was carried out. While aminonitriles from glycal and 2-deoxy-beta-D-glycosyl aldehydes were prepared in satisfactory yields, lower yields were obtained with C-glycosyl aldehydes. Strecker reaction with the benzyl-protected 1-C-formyl-D-galactal and S- or R-1-phenylethylamine (S-PEA or R-PEA) yielded predominantly the R-configured C-glycosyl aminoacetonitrile. The direction of the nucleophilic addition appears to be governed by the configuration of the anomeric carbon with beta-linked sugars. Since the stereochemistry of the transition state is unknown according to the configuration of the major product a Felkin-Ahn selectivity can be mainly presumed. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis studies of structural analogues of tagetitoxin: 2-phosphate
  作者：Barry R. Dent、Richard H. Furneaux、Graeme J. Gainsford、Gregory P. Lynch

  DOI：10.1016/s0040-4020(99)00327-0

  日期：1999.5

  Synthetic approaches to structural analogues of tagetitoxin (1) are described. The successful route to analogue 3 (X=O) has, as a key step, protection of the cis-vicinal amino alcohol moiety of compound 7 as an N-benzylated cyclic carbamate (9). X-Ray crystallographic analyses of the hydrochloride of compound 7 and of the hydroxyacid 56 are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.