5-deoxy-1,2-O-(1-isopropylidene)-3-O-benzyl-α-D-xylohexofuranonitrile | 131053-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-deoxy-1,2-O-(1-isopropylidene)-3-O-benzyl-α-D-xylohexofuranonitrile
• 英文别名: 3-O-benzyl-5-cyano-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose；2-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]acetonitrile
• CAS: 131053-22-0
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: OTAZBDNXBIHEAC-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-deoxy-1,2-O-(1-isopropylidene)-3-O-benzyl-α-D-xylohexofuranonitrile 生成 methyl 3-O-benzyl-5-cyano-5-deoxy-α-D-xylofuranoside
  参考文献：
  名称：

  FLEET, GEORGE W. J.;WITTY, DAVID R., TETRAHEDRON: ASYMMETRY, 1,(1990) N, C. 119-136

  摘要：

  DOI：
• 作为产物：
  描述：

  溴甲苯 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 水 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 5-deoxy-1,2-O-(1-isopropylidene)-3-O-benzyl-α-D-xylohexofuranonitrile
  参考文献：
  名称：

  Synthesis of homochiral β-hydroxy-α-aminoacids [(2S,3R,4R)-3,4-dihydroxyproline and (2S,3R,4R)-3,4-dihydroxypipecolic aicd] and of 1,4-dideoxy-1,4-imino-D-arabinitol [DAB1] and fagomine [1,5-imino-1,2,5-trideoxy-D-arabino-hexitol]

  摘要：

  DOI：

  10.1016/s0957-4166(00)86337-5

文献信息

• Synthesis of chiral pyrrolidine and piperidine glycosidase inhibitors
  申请人：Monsanto Company

  公开号：US05013842A1

  公开（公告）日：1991-05-07

  There is disclosed a novel method for the syntheses of chiral pyrrolidines and piperidines by the intramolecular ring closure of anomeric mixtures of 4-amino- and 5-amino-2-trifluoromethanesulfonates of methyl furanosides. The novel method preferably provides for the efficient syntheses from diacetone glucose of 1,4-dideoxy-1,4-imino-D-arabinitol--known as DAB1, (2S,3R,4R)-3,4-dihydroxyproline, fagomine [1,5-imino-1,2,5-trideoxy-D-arabino-hexitol], and (2S,3R,4R)-3,4-dihydroxypipecolic acid by intramolecular nucleophilic displacement by an amino function of 2-O-trifluoromethanesulphonates of anomeric mixtures of methyl furanosides.

  本发明揭示了一种新颖的方法，通过对甲基呋喃苷的4-氨基和5-氨基-2-三氟甲磺酸酯的异构混合物进行分子内环闭合，合成手性吡咯烷和哌啶。这种新方法优选地提供了从双丙酮葡萄糖合成1,4-二去氧-1,4-亚胺-D-阿拉伯糖醇（称为DAB1）、（2S,3R,4R）-3,4-二羟基脯氨酸、法果胺[1,5-亚胺-1,2,5-三去氧-D-阿拉伯糖醇]以及（2S,3R,4R）-3,4-二羟基哌酰胺的高效合成，通过对甲基呋喃苷的异构混合物的2-O-三氟甲基磺酸酯的分子内亲核取代反应实现。
• Metal-Free Iodine-Mediated Deoxygenation of Alcohols in the Position α to Electron-Withdrawing Groups
  作者：Maëva M. Pichon、Fabien Stauffert、Luis G. Addante-Moya、Anne Bodlenner、Philippe Compain

  DOI：10.1002/ejoc.201800051

  日期：2018.4.9

  The use of a substoichiometric amount of molecular iodine in the presence of PPh3 and pyridine effects a direct deoxygenation of primary and secondary alcohols in positions α to a variety of activating electron‐withdrawing groups, including ketones, esters, amides, imides and nitrile groups.

  在 PPh3 和吡啶的存在下，使用亚化学计量的分子碘可将 α 位的伯醇和仲醇直接脱氧为各种活化的吸电子基团，包括酮、酯、酰胺、酰亚胺和腈基。
• A Novel Deoxygenation of Hydroxy Groups Activated by a Vicinal Carbonyl Group <i>via</i> Reaction with Ph₃P/I₂/Imidazole
  作者：Amélia P. Rauter、Ana C. Fernandes、José A. Figueiredo

  DOI：10.1080/07328309808001882

  日期：1998.9.1

  A new procedure for a direct conversion of an alpha-hydroxy sugar ester, lactone or amide into the corresponding alpha-deoxyester , lactone or nitrile using the system Ph-3/I-2 /imidazole is reported. Its efficiency is illustrated by deoxygenation in good yields at position 2 of methyl 3,4:5,6-di-O-isopropylidene-D-gluconate (1), and at positions 5 of 3-O-benzyl-1,2-O-isopropylidene-alpha-D-glucofuranuronamide (3) and 1,2-O-isopropylidene-alpha-D-glucofuranurono-6,3-lactone (5). Reaction with 5,6-O-isopropylidene-L- and -D-gulo-1,4-lactones (7) and (9), respectively, afforded the corresponding alpha,beta-unsaturated lactones in good yields.
• FLEET, GEORGE W. J.;WITTY, DAVID R., TETRAHEDRON: ASYMMETRY, 1,(1990) N, C. 119-136
  作者：FLEET, GEORGE W. J.、WITTY, DAVID R.

  DOI：——

  日期：——
• US5013842A
  申请人：——

  公开号：US5013842A

  公开（公告）日：1991-05-07