β-D-glucopyranosyl cyanide | 3737-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-glucopyranosyl cyanide
• 英文别名: 1-β-cyano-D-glucose；beta-D-Glucopyranosyl cyanide；(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-carbonitrile
• CAS: 3737-60-8
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: NNWGBANFKDPMSI-PJEQPVAWSA-N

物化性质

• 熔点：
  90-92 °C(Solv: water (7732-18-5))
• 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-glucopyranosyl cyanide 在 cobalt(II) chloride sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 以63%的产率得到β-D-glucopyranosylmethylamine
  参考文献：
  名称：

  Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides

  摘要：

  [GRAPHICS]Reported herein is a general method for the efficient syntheses of a variety of beta -cyano glycosides through the activation of per-O-trimethylsllyl glycosides with TMSI to form alpha -glycosyl iodides, which undergo S(N)2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)(6) in THF/H2O to give the corresponding aminomethyl glycosides.

  DOI：

  10.1021/ol0160405
• 作为产物：
  描述：

  3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-gulo-heptononitrile 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 β-D-glucopyranosyl cyanide
  参考文献：
  名称：

  重氮甲基β-d-吡喃半乳糖基和β-d-吡喃葡萄糖基酮的合成。碳水化合物结合蛋白的潜在亲和标记试剂

  摘要：

  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。

  DOI：

  10.1016/s0008-6215(00)90295-7

文献信息

• Synthesis of 2-(β-d-glucopyranosyl)-5-(substituted-amino)-1,3,4-oxa- and -thiadiazoles for the inhibition of glycogen phosphorylase
  作者：Béla Szőcs、Marietta Tóth、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.carres.2013.03.009

  日期：2013.11

  syl)formaldehyde]semicarbazone was prepared in the reaction of O-perbenzoylated β-d-glucopyranosyl cyanide and 4-phenylsemicarbazide in the presence of Raney-Ni. Acylation of O-perbenzoylated C-(β-d-glucopyranosyl)formaldehyde semicarbazone furnished the corresponding 4-acyl-[C-(β-d-glucopyranosyl)formaldehyde]semicarbazones. The reaction of O-perbenzoylated C-(β-d-glucopyranosyl)formaldehyde semicarbazone

  在阮内镍的存在下，通过邻苯甲酰化β-d-吡喃葡萄糖基氰化物与4-苯并氨基脲进行邻苯甲酰化的4-苯基-[C-（β-d-吡喃葡萄糖基）甲醛]半卡巴zone的制备。O-过苯甲酰化的C-（β-d-吡喃葡萄糖基）甲醛半卡巴zone的酰化作用提供了相应的4-酰基-[C-（β-d-吡喃葡萄糖基）甲醛]半卡巴唑酮。O-过苯甲酰化的C-（β-d-吡喃葡萄糖基）甲醛半卡巴zone与相应的硫代氨基脲的反应产生了O-过苯甲酰化的C-（β-d-吡喃葡萄糖基）甲醛丁硫缩氨基脲及其4-苯基衍生物。O-过苯甲酰化的C-（β-d-吡喃葡萄糖基）甲醛硫代半碳zone的酰化提供相应的4-酰基-2-酰基氨基-5-（β-d-吡喃葡萄糖基）-Δ（2）-1,3,4-噻二唑烷。这些前体的氧化转化得到O-保护的2-（β-d-吡喃葡萄糖基）-5-取代的氨基-1,3,4-氧杂-和噻二唑。在碱催化的酯交换条件下除去O-苯甲酰基保护基。C-吡喃葡
• 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.
• Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-<i>O</i>-silylated Mono- and Disaccharides
  作者：Abhijit S. Bhat、Jacquelyn Gervay-Hague

  DOI：10.1021/ol0160405

  日期：2001.6.1

  [GRAPHICS]Reported herein is a general method for the efficient syntheses of a variety of beta -cyano glycosides through the activation of per-O-trimethylsllyl glycosides with TMSI to form alpha -glycosyl iodides, which undergo S(N)2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)(6) in THF/H2O to give the corresponding aminomethyl glycosides.
• 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。