6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,3,4,5-tetradeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undecitol | 443916-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,3,4,5-tetradeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undecitol
• 英文别名: tert-butyl (4S)-2,2-dimethyl-4-[3-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propyl]-1,3-oxazolidine-3-carboxylate
• CAS: 443916-01-6
• 化学式: C₄₇H₅₉NO₈
• 分子量: 765.987
• InChiKey: UXLYZEDZJWCNTD-QKQXSSCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  56
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,3,4,5-tetradeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undecitol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以93%的产率得到6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,3,4,5-tetradeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undeconic acid
  参考文献：
  名称：

  Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (C-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde Coupling

  摘要：

  A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of alpha- or beta-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-alpha-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of alpha- and beta-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.

  DOI：

  10.1021/jo020054m
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethyne 在 4-二甲氨基吡啶 、 正丁基锂 、 sodium acetate 、 N,N'-硫羰基二咪唑 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 11.0h， 生成 6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,3,4,5-tetradeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undecitol
  参考文献：
  名称：

  General, stereoselective synthesis of ethylene isosteres of α- and β-glycosylasparagines

  摘要：

  The coupling of alpha- or beta-D-linked lithium C-glycosyl acetylides with N-Boc D-serinal acetonide followed by the reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring afforded alpha- and beta-anomer pairs of C-glycosyl alpha-aminopentanoic acids (gluco, manno, galacto, and 2-acetamido-galacto). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00403-2