2,3,4-tri-O-acetyl-β-L-fucopyranosyl cyanide | 86651-64-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-β-L-fucopyranosyl cyanide
• 英文别名: 2,3,4-tri-O-acetyl-α-L-fucopyranosyl cyanide；[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-cyano-2-methyloxan-3-yl] acetate
• CAS: 86651-64-1
• 化学式: C₁₃H₁₇NO₇
• 分子量: 299.28
• InChiKey: FZNCABDRPGXWPZ-WSBJEXOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-β-L-fucopyranosyl cyanide 在 palladium on activated charcoal 吡啶 、 1,4-bis(methylamino)pyridine 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 70.0 ℃ 、8.27 MPa 条件下， 反应 84.0h， 生成 N-(2,3,4-tri-O-acetyl-α-L-fucopyranosylmethyl)-acetamide
  参考文献：
  名称：

  Palladium−Charcoal-Catalyzed Reduction of Tri-O-acetyl-β-l-Fucopyranosyl Cyanide:  A Route to Small Cluster Oligosaccharide Mimetics (SCOMs)

  摘要：

  Synthesis of glycosyl cyanides was optimized with a new catalyst system. Reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide with Pd-hydrogen, in the presence of Ac2O and Boc(2)O, gave N-protected-mono- and -di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl)-amines, which allow for the syntheses of small cluster oligosaccharide mimetics of fucopyranosylomethyl-substituted ureas. From di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl) amine was also prepared a carbamoyl chloride as a potentially useful synthon for preparation of more complex C-glycosidic conjugates.

  DOI：

  10.1021/ol020123j
• 作为产物：
  描述：

  1,2,3,4-tetra-O-trimethylsilyl-α-L-fucopyranose 在 4-二甲氨基吡啶 吡啶 、 甲醇 、 molecular sieve 、 碘代三甲硅烷 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 9.84h， 生成 2,3,4-tri-O-acetyl-β-L-fucopyranosyl cyanide
  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

文献信息

• Synthesis and characterization of some anomeric pairs of per-O-acetylated aldohexopyranosyl cyanides (per-O-acetylated 2,6-anhydroheptononitriles). On the reaction of per-O-acetylaldohexopyranosyl bromides with mercuric cyanide in nitromethane
  作者：Robert Walter Myers、Yuan Chuan Lee

  DOI：10.1016/0008-6215(84)85065-x

  日期：1984.9

  per-O-acetylaldohexopyranosyl cyanides of D-galactose, L-fucose, D-glucose, and D-mannose, as well as of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl cyanide, are described. Cyanation of the readily available, per-O-acetylaldohexopyranosyl bromides with mercuric cyanide in nitromethane, and subsequent purification, gave the corresponding, crystalline glycosyl cyanides with a high degree of

  D-半乳糖，L-岩藻糖，D-葡萄糖和D-甘露糖以及3,4,6-三-O-乙酰-描述了2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖基氰化物。在硝基甲烷中将氰化汞与现成的全-O-乙酰基醛基吡喃并吡喃糖基溴化物氰化，然后纯化，得到相应的结晶的糖基氰基氰化物，具有较高的1,2-反式立体选择性。因此，以20至79％的产率获得1,2-反式构型的全-O-乙酰化的醛-己二吡喃喃糖基氰化物，而以小于或等于8.4％的产率获得相应的1,2-顺式异构体。如此制备的1,2-反式：1,2-顺式端基异构体的比例大于或等于8.5：1。这些不可逆的氰化反应的主要副产物是全-O-乙酰化的1,2-O- [1-（异氰基和内氰基）亚乙基] aldohexopyranoses，得率高达40％。通过元素分析，化学转化，振动光谱以及13C和1H核磁共振光谱明确地确定了每个O-乙酰基乙二醛-吡喃并吡喃糖基氰化物的结构分配。描述了这些C
• Efficient stereocontrolled synthesis of C-glycosides using glycosyl donors substituted by propane 1,3-diyl phosphate as the leaving group
  作者：Gurdial Singh、Hariprasad Vankayalapati

  DOI：10.1016/s0957-4166(01)00305-6

  日期：2001.7

  a- and beta -Glycosyl cyanides, per-O-acetyl-1,2-O-1-cyanoethylidenes and C-allyl glycopyranosides were efficiently prepared by treatment of 2,3,4-tri-O-acetyl-alpha,beta -L-rhamno-, L-fuco- and 2,3,4,6-tetra-O-acetyl-alpha,beta -D-galactopyranosyl propane-1,3-diyl phosphates with trimethylsilyl cyanide (TMSCN) and allyltrimethylsilane in the presence of trimethylsilyl triflate (TMSOTf). Similarly 2,3,4,6-tetra-O-benzyl-alpha,beta -D-manno- and D-glucopyranosyl propane-1,3-diyl phosphates were employed in the synthesis of C-glycosides. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Frische, Klaus; Schmidt, Richard R., Liebigs Annalen der Chemie, 1994, # 3, p. 297 - 304
  作者：Frische, Klaus、Schmidt, Richard R.

  DOI：——

  日期：——