2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline | 117177-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline
• 英文别名: (3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-3a,5,6,6a-tetrahydrofuro[3,2-d][1,3]oxazol-6-ol
• CAS: 117177-19-2
• 化学式: C₁₁H₁₇NO₅
• 分子量: 243.26
• InChiKey: BLASPHDBCPYTRC-IGORNWKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 在 palladium hydroxide - carbon 盐酸 、 氢气 、 溴 、 三正丁基甲氧基锡 、 二正丁基氧化锡 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 甲醇 、 硫酸 、 水 、 溶剂黄146 为溶剂， -15.0~60.0 ℃ 、101.33 kPa 条件下， 反应 352.25h， 生成 2-乙酰氨基-1,2,5-三脱氧-1,5-亚氨基-d-葡萄糖醇
  参考文献：
  名称：

  2-Acetamido-1,2-dideoxynojirimycin: an improved synthesis

  摘要：

  The potent beta-N-acetylglucosaminidase inhibitor, 2-acetamido-1,2-dideoxynojirimycin, was prepared in 6 steps from N-acetyl-D-glucosamine (overall yield 10%) via the double reductive amination of a keto aldehyde as the key step.

  DOI：

  10.1016/s0040-4020(01)80229-5
• 作为产物：
  描述：

  D-GlcNAc 生成 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline
  参考文献：
  名称：

  MACK, HANS;BASABE, JAVIER VILLALVA;BROSSMER, REINHARD, CARBOHYDR. RES., 175,(1988) N 2, 311-316

  摘要：

  DOI：

文献信息

• Novel O-acetylated decasaccharides
  申请人：Institut Pasteur

  公开号：EP2386563A1

  公开（公告）日：2011-11-16

  The present invention relates to diversely acetylated decasaccharides of formula (I) representative of two repeating units of Shigella flexneri serotype 2a O-antigen, conjugates and method of preparation thereof. These compounds exhibit antigenic properties and are particularly useful for the diagnosis of Shigella infection. wherein R1 and R2 are as defined in claim 1.

  本发明涉及式(I)的多样乙酰化十糖，代表志贺氏菌弗氏氏2a O-抗原的两个重复单元，以及其结合物和制备方法。这些化合物具有抗原性质，特别适用于志贺氏菌感染的诊断。 其中R1和R2如权利要求1中定义的。
• Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization
  作者：Laxminarayan Sahoo、Anadi Singhamahapatra、Satyanarayan Sahoo

  DOI：10.2298/jsc170905030s

  日期：——

  A series of novel 1,3-difunctionalized glycoconjugates were synthe­sized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 function­aliz­ation of sugar molecules was achieved by chemical functionalization of iso­pro­pylidene or oxazoline protected sugar derivatives. The structural diversity at the anomeric carbon was

  使用D-葡萄糖和D-GlcNAc的区域选择性官能化和立体选择性糖苷化的序列，合成了一系列新型的1，3-双官能化的糖缀合物。糖分子的区域选择性C-3功能化是通过异亚丙基或恶唑啉保护的糖衍生物的化学功能化实现的。通过立体选择性化学糖苷化探索了异头碳的结构多样性。恶唑啉保护的D-GlcNAc衍生物根据使用的路易斯酸的量，在糖基化反应中产生吡喃糖或呋喃糖衍生物。具有叠氮化物或炔基的多样化官能化的糖缀合物潜在地可用于通过点击反应合成多功能复合糖缀合物。
• Nucleophilic Aromatic Substitution (S_NAr) as an Approach to Challenging Carbohydrate–Aryl Ethers
  作者：Alexander S. Henderson、Sandra Medina、John F. Bower、M. Carmen Galan

  DOI：10.1021/acs.orglett.5b02413

  日期：2015.10.2

  A general and practical route to carbohydrate–aryl ethers by nucleophilic aromatic substitution (SNAr) is reported. Upon treatment with KHMDS, C–O bond formation occurs between carbohydrate alcohols and a diverse range of fluorinated (hetero)aromatics to provide the targets in good to excellent yields. Commercially available arylating agents, high atom economy, and high regioselectivity are notable

  据报道，通过亲核芳族取代（S N Ar）制取碳水化合物-芳基醚的通用方法是可行的。用KHMDS处理后，碳水化合物醇与各种氟化（杂）芳烃之间便会形成C–O键，从而以良好至极佳的收率提供了目标化合物。该方案的显着特征是可商购的芳基化剂，高原子经济性和高区域选择性。芳族醚产物具有广泛用途的潜力，如合成新型手性P，N-配体所举例说明的。
• Regioselective Glycosylation of Glucosamine and Galactosamine Derivates Using O-Pivaloyl Galactosyl Donors
  作者：Mathia Oßwald、Uwe Lang、Siglinde Friedrich-Bochnitschek、Waldemar Pfrengle、Horst Kunz

  DOI：10.1515/znb-2003-0808

  日期：2003.8.1

  Penta-O-pivaloyl-galactopyranose and tetra-O-pivaloyl-galactopyranosyl bromide after electrophilic activation reacted with 6-O-protected 2-azido-galactosides to give the precursor structures of the Thomsen-Friedenreich antigen disaccharide with high regioselectivity, but low yield.With 4,6-Obenzylidene protected 2-azidogalactosides and 2-O-pivaloyl phenylthio galactosides, T-antigen disaccharides of this type were obtained in good yields. Glycosylation reactions of 4,6-O-benzylidene protected glucosamine derivatives with O-pivaloyl protected galactosyl bromide efficiently gave lactolactosamine disaccharides. Even a thioglycoside was efficiently galactosylated by this method resulting in the formation of a disaccharide thioglycoside useful itself as a potential glycosyl donor.

  Penta-O-pivaloyl-galactopyranose和tetra-O-pivaloyl-galactopyranosyl溴在亲电活化后与6-O-保护的2-azido-galactosides反应，高选择性地形成Thomsen-Friedenreich抗原二糖的前体结构，但产率较低。使用4,6-Obenzylidene保护的2-azidogalactosides和2-O-pivaloyl苯硫基半乳苷，可以得到这种类型的T-抗原二糖，产率较高。4,6-O-benzylidene保护的葡萄糖氨基衍生物与O-pivaloyl保护的半乳苷溴的糖基化反应有效地产生了乳糖氨二糖。甚至通过这种方法，一种硫代糖苷也可以有效地被半乳苷化，形成一种作为潜在糖基供体的二糖硫代糖苷。
• A facile two-step synthesis of N-acetylmuramic acid by selective functionalization of HO-3 of 2-acetamido-2-deoxy-d-glucose
  作者：Hans Merten、Reinhard Brossmer

  DOI：10.1016/0008-6215(89)85055-4

  日期：1989.8

  Synthese d'acide N-acetyl muramique protege ou non a partir d'un derive de furo [2,1.d] oxazoline

  合成d'酰胺N-乙酰基muramique蛋白质或衍生品[2,1.d]恶唑啉