1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranose | 264881-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranose
• 英文别名: (3S,4S,5R)-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranose acetate；3,4,6-Tri-O-benzyl-2-deoxy-D-arabino-hexopyranosyl acetate；Acetyl 3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranoside；1-O-acetyl-3,4,6 tri-O-benzyl-D-glucose；(4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl acetate；3,4,6-tri-O-benzyl-2-deoxy-1-O-acetyl-α/β-D-glucopyranose；1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose；1-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose；[(4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] acetate
• CAS: 264881-65-4
• 化学式: C₂₉H₃₂O₆
• 分子量: 476.569
• InChiKey: AIWFPMIKISNJRA-ZTTQFBNESA-N

物化性质

• 沸点：
  587.3±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranose 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 14.25h， 生成 methyl (4,5,7-tri-O-benzyl-2,3-dideoxy-α-D-arabino-hept-2-ulopranosid)onate
  参考文献：
  名称：

  Regioselective synthesis of naphthoquinone/naphthoquinol–carbohydrate hybrids by [4 + 2] anionic annulations and studies on their cytotoxicity

  摘要：

  一种新颖的方法用于合成萘醌/萘醌醇-碳水化合物混合物，其中Hauser环化反应被描述为关键的合成步骤。

  DOI：

  10.1039/c6ob02154a
• 作为产物：
  描述：

  溴甲苯 在 氢溴酸 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranose
  参考文献：
  名称：

  通过糖苷的多功能 C(sp3)−H 糖基化合成 C-寡糖

  摘要：

  公开了钯催化的糖苷的C(sp 3 )-H糖基化。这种通过C(sp 3 )−H糖基化组装的糖具有优异的位点选择性和立体选择性，能够有效合成多种C-二糖和C-三糖。

  DOI：

  10.1002/anie.202114993

文献信息

• Additive‐Free Gold(III)‐Catalyzed Stereoselective Synthesis of 2‐Deoxyglycosides Using Phenylpropiolate Glycosides as Donors
  作者：Mukta Shaw、Amit Kumar

  DOI：10.1002/asia.201900888

  日期：2019.12.13

  Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields

  在无外部添加剂的条件下，使用金（III）盐作为催化剂，可从台式稳定且易于合成的脱氧苯丙酸丙二醇酯（D-PPGs）中实现脱氧糖苷的立体选择性合成。在简单的催化系统下，D-PPG与多种糖和非糖受体反应，以高至优异的收率产生主要的α-立体选择性O / N-脱氧糖苷，并再生易于分离和重用的苯丙酸。在优化的反应条件下，含有武装和解除武装团体的脱氧PPG能够很好地存活。另外，展示了D-PPG的正交性质，并且还合成了1，1'-连接的海藻糖型糖。
• Zinc mediated activation of terminal alkynes: stereoselective synthesis of alkynyl glycosides
  作者：Madhu Babu Tatina、Anil Kumar Kusunuru、Syed Khalid Yousuf、Debaraj Mukherjee

  DOI：10.1039/c4ob01405g

  日期：——

  mediated alkynylation reaction was studied for the preparation of C-glycosides from unactivated alkynes. Different glycosyl donors such as glycals and anomeric acetates were tested towards an alkynyl zinc reagent obtained from alkynes using zinc dust and ethyl bromoacetate as an additive. The method provides simple, mild and stereoselective access to alkynyl glycosides both from aromatic and aliphatic acetylenes

  研究了锌介导的炔基化反应，用于从未活化的炔烃制备C-糖苷。使用锌粉和溴乙酸乙酯作为添加剂，对从炔烃制得的炔基锌试剂进行了测试，测试了不同的糖基供体（例如，乙二醇和异头乙酸酯）。该方法提供了从芳族和脂族乙炔对炔基糖苷的简单，温和和立体选择。
• Preparation of THP‐Ester‐Derived Pyridinium‐Type Salts and their Reactions with Various Nucleophiles
  作者：Hiromichi Fujioka、Yutaka Minamitsuji、Takahiro Moriya、Kazuhisa Okamoto、Ozora Kubo、Tomoyo Matsushita、Kenichi Murai

  DOI：10.1002/asia.201200234

  日期：2012.8

  cis‐pyridinium‐type salts. These salts reacted with various nucleophiles, such as alcohols, azides, and organozinc reagents, to form nucleophilic‐substitution products. A characteristic feature of these processes was that they took place under mild conditions, which did not affect acid‐labile protecting groups. Furthermore, the reactions that employed azides and C‐nucleophiles generated 2,6‐trans products with high

  已经开发了通过吡啶鎓型盐中间体进行的四氢吡喃基（THP）和相关的碳水化合物衍生的酯的异头位置的亲核取代。用TMSOTf（TMS =三甲基甲硅烷基）和2-取代的吡啶（例如2-对-甲苯基吡啶和2-甲氧基吡啶）处理6-取代的α-乙酰氧基-四氢吡喃可有效产生顺式py型盐。这些盐与各种亲核试剂（例如醇，叠氮化物和有机锌试剂）反应，形成亲核取代产物。这些过程的一个特征是它们发生在温和的条件下，并不影响对酸不稳定的保护基团。此外，使用叠氮化物和C-亲核试剂的反应生成具有高立体选择性的2,6-反式产物。
• Reactions of Difluoroenoxysilanes with Glycosyl Donors: Synthesis of Difluoro-C-glycosides and Difluoro-C-disaccharides
  作者：Hatice Berber、Thierry Brigaud、Olivier Lefebvre、Richard Plantier-Royon、Charles Portella

  DOI：10.1002/1521-3765(20010216)7:4<903::aid-chem903>3.0.co;2-m

  日期：2001.2.16

  trifluoromethyltrimethylsilane under fluoride activation, were glycosylated with some glycosyl donors (acylglycosides, glycals) to yield difluoro-C-glycosides with a difluoromethylene group in the place of the anomeric oxygen. This reaction strongly depends on the substituent in the 2-position of the glycosyl donor. Application of this methodology to a xylose-derived acylsilane led to the formation

  由酰基硅烷和三氟甲基三甲基硅烷在氟化物活化下制得的二氟烯氧基硅烷与某些糖基供体（酰基糖苷，糖基）进行糖基化反应，制得具有二氟亚甲基基团的异氟-C-糖苷代替异头氧。该反应强烈取决于糖基供体2-位的取代基。该方法在木糖衍生的酰基硅烷上的应用导致形成了二氟-C-二糖，是一种等排的O-糖基模拟物。
• Reinvestigation of the mercuration–demercuration reaction on alkylated glycals: an improved method for the preparation of 2,3-dideoxy-α,β-unsaturated carbohydrate enals
  作者：Ram Sagar、Rashmi Pathak、Arun K Shaw

  DOI：10.1016/j.carres.2004.05.027

  日期：2004.8

  Abstract Alkyl protected glycals can be easily converted into their corresponding α,β-unsaturated enals (Perlin aldehydes) in good to very good yields by reaction with HgSO 4 and aqueous 0.02 N H 2 SO 4 in THF or 1,4-dioxane. While the formation of Perlin aldehydes from benzyl-protected glucal and arabinal was accomplished by refluxing the reaction mixture in 1,4-dioxane, the benzyl-protected galactal

  摘要与HgSO 4和0.02 NH 2 SO 4水溶液在THF或1,4-二恶烷中反应，可以很容易地将烷基保护的糖轻松地转化为相应的α，β-不饱和烯醛（Perlin醛）。通过将反应混合物在1,4-二恶烷中回流来完成由苄基保护的葡糖醛和阿拉伯糖生成Perlin醛的过程，而苄基保护的半乳糖和甲基保护的葡糖醛，半乳糖和阿拉伯糖在室温下从该反应中产生醛使用THF或1,4-二恶烷作为溶剂。