5-叠氮基-5-脱氧-1,2-o-异亚丙基-beta-D-果糖 | 94801-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-叠氮基-5-脱氧-1,2-o-异亚丙基-beta-D-果糖
• 中文别名: 5-叠氮基-5-脱氧-1,2-O-亚异丙基B-D-果糖
• 英文名称: 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose
• 英文别名: 5-azido-5-deoxy-1,2-O-isopropylidene-β-L-sorbopyranose；5-azido-5-deoxy-D-fructose 1,2-acetonide；5-Azido-5-deoxy-1,2-O-isopropylidene-beta-D-fructose；(5S,6S,7R,8R)-8-azido-2,2-dimethyl-1,3,10-trioxaspiro[4.5]decane-6,7-diol
• CAS: 94801-01-1
• 化学式: C₉H₁₅N₃O₅
• 分子量: 245.235
• InChiKey: GYSFIJJRAZOESF-JAKMQLQISA-N

物化性质

• 熔点：
  108-109°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  5-叠氮基-5-脱氧-1,2-o-异亚丙基-beta-D-果糖 在 palladium on activated charcoal 吡啶 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、400.0 kPa 条件下， 反应 48.0h， 生成 (2R,3R,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)-N-phenylpyrrolidine-1-carbothioamide
  参考文献：
  名称：

  Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases

  摘要：

  Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp(2)-hybridized endocyclic ring nitrogen.

  DOI：

  10.1021/jo0499221
• 作为产物：
  描述：

  (-)-3-deoxy-1,2:4,5-di-O-isopropylidene-β-D-fructofuranos-3-yl benzoate 在 吡啶 、 咪唑 、 六甲基磷酰三胺 、 sodium azide 、 碘 、 sodium methylate 、 溶剂黄146 、 三苯基膦 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 4.5h， 生成 5-叠氮基-5-脱氧-1,2-o-异亚丙基-beta-D-果糖
  参考文献：
  名称：

  Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases

  摘要：

  Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp(2)-hybridized endocyclic ring nitrogen.

  DOI：

  10.1021/jo0499221

文献信息

• Controlled Garegg Conditions for Selective Iodination on Pyranose Templates
  作者：Ana-Catarina Simao、Sandrina Silva、Amelia P. Rauter、Patrick Rollin、Arnaud Tatibouët

  DOI：10.1002/ejoc.201001325

  日期：2011.4

  Regio- and stereoselective iodinations under controlled Garegg conditions were performed on vicinal diols and contiguous triols located on pyranose templates. P- D -Fructo- or psicopyranose-based diols were selectively iodinated at C-5 or C-4, respectively, to afford the L -sorbo or D -tagato iodohydrins. In contrast, the related triols only underwent selective iodination at C-5. Application of the

  在受控的 Garegg 条件下，对位于吡喃糖模板上的邻二醇和连续三醇进行区域选择性和立体选择性碘化。基于 P-D-果糖或吡喃吡喃糖的二醇分别在 C-5 或 C-4 处选择性碘化，以提供 L-山梨糖或 D-塔格托碘醇。相比之下，相关的三醇仅在 C-5 处进行选择性碘化。将该方法应用于 D-葡糖苷和 D-吡喃半乳糖苷导致分别在 C-3 或 C-4 处选择性碘化，以提供 D-allo 或 D-葡糖碘醇。
• .alpha.-Amino aldehyde equivalents as substrates for rabbit muscle aldolase: synthesis of 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine
  作者：Rebecca R. Hung、Julie Ann Straub、George M. Whitesides

  DOI：10.1021/jo00012a015

  日期：1991.6

  This work examined the application of rabbit muscle aldolase (RAMA) to stereospecific carbon-carbon bond formation in the preparation of carbohydrates containing amino groups. Several alpha-amino aldehyde equivalents were evaluated as substrates for RAMA and for their synthetic utility in transformations following the aldol reaction. This methodology is illustrated by the syntheses of the pyrrolidine alkaloids 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R), 4(R)-dihydroxypyrrolidine. The kinetic resolution of racemic aldehydes by RAMA and mild methods for transforming the amino equivalents into the desired amines are discussed briefly.
• d-Fructose–l-sorbose interconversions. Access to 5-thio-d-fructose and interaction with the d-fructose transporter, GLUT5
  作者：Arnaud Tatibouët、Myriam Lefoix、Jonathan Nadolny、Olivier R Martin、Patrick Rollin、Jing Yang、Geoffrey D Holman

  DOI：10.1016/s0008-6215(01)00153-7

  日期：2001.7

  Epimerisation and subsequent functionalization at C-5 of D-fructopyranose derivatives under Mitsunobu and Garegg's conditions provided efficient access to 5-thio-D-fructose (2) as well as to 5-azido-5-deoxy-1,2-O-isopropylidene-beta -D-fructopyranose (19), a known precursor to 2,5-deoxy-2,5-imino-D-mannitol (3). The interaction of 2 with the D-fructose transporter GLUTS, was found to be weaker than that of D-fructose, a result that suggests involvement of the ring oxygen atom in the recognition of D-fructose by GLUTS. (C) 2001 Elsevier Science Ltd. All rights reserved.
• HUNG, REBECCA R.;STRAUB, JULIE ANN;WHITESIDES, GEORGE M., J. ORG. CHEM., 56,(1991) N2, C. 3849-3855
  作者：HUNG, REBECCA R.、STRAUB, JULIE ANN、WHITESIDES, GEORGE M.

  DOI：——

  日期：——
• Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases
  作者：M. Isabel García-Moreno、David Rodríguez-Lucena、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1021/jo0499221

  日期：2004.5.1

  Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp(2)-hybridized endocyclic ring nitrogen.