prop-2-ynyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside | 214333-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: prop-2-ynyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-ynoxyoxane
• CAS: 214333-72-9
• 化学式: C₃₇H₃₈O₆
• 分子量: 578.705
• InChiKey: ATGYINYFSVYATO-WNRBQEJJSA-N

物化性质

• 沸点：
  693.8±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  prop-2-ynyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 在 potassium tert-butylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.0h， 以84%的产率得到allenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Study of metal and acid catalysed deprotection of propargyl ethers of alcohols via their allenyl ethers

  摘要：

  A new method for the deprotection of prop-2-ynyl ethers 1b-9b is described. Isomerisation of 1b-9b to O-allenyl ethers 1d-9d and deprotection by reaction with Hg(OCOCF3)(2), aq.HCl, aq.CF3CO2H and best by use of a catalytic amount of OsO4 is described to obtain the alcohols 1a-9a in good yield. Application of this method for the deprotection of prop-2-enyl ethers 7c,8c,10c-13c via their corresponding prop-1-enyl ethers 7e,8e,10e-13e to obtain the corresponding alcohols 7a,8a,10a-13a is also described, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00631-6
• 作为产物：
  描述：

  2-propynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 prop-2-ynyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Design, Development and Utility of Glycosyl Donors Bearing an Acetoxymethoxy Leaving Group

  摘要：

  已制备新型糖苷供体 2d、4d 和 6d，具有“乙酰氧基-甲氧基”离去基团，并通过将其与醇 A-G 结合，利用 BF3-Et2O 作为促使剂，展示了它们的实用性，从而获得了二糖和三糖。

  DOI：

  10.1246/cl.1998.863

文献信息

• Cooperative Catalysis in Glycosidation Reactions with<i>O</i>-Glycosyl Trichloroacetimidates as Glycosyl Donors
  作者：Yiqun Geng、Amit Kumar、Hassan M. Faidallah、Hassan A. Albar、Ibrahim A. Mhkalid、Richard R. Schmidt

  DOI：10.1002/anie.201302158

  日期：2013.9.16

  Thiourea mediates cooperative glycosidation through hydrogen bonding. N,N′‐Diarylthiourea as cocatalyst enforces an SN2‐type acid‐catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From O‐(α‐glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, β‐glycosides are preferentially or exclusively obtained.

  硫脲通过氢键介导协同糖基化。N，N'-二芳基硫脲作为助催化剂即使在室温下也可增强S N 2型酸催化的糖苷化作用（见方案； Bn =苄基）。从O-（α-糖基）三氯乙酰亚氨酸盐作为糖基供体和各种受体，可以优先或仅从中获得β-糖苷。
• Design, Development and Utility of Glycosyl Donors Bearing an Acetoxymethoxy Leaving Group
  作者：Hari Babu Mereyala、Srinivas Reddy Gurrala

  DOI：10.1246/cl.1998.863

  日期：1998.9

  Novel glycosyl donors 2d, 4d and 6d bearing an ‘acetoxy methoxy’ leaving group have been prepared and their utility is shown by coupling them with alcohols A-G to obtain di- and trisaccharides by use of BF3-Et2O as a promoter.

  已制备新型糖苷供体 2d、4d 和 6d，具有“乙酰氧基-甲氧基”离去基团，并通过将其与醇 A-G 结合，利用 BF3-Et2O 作为促使剂，展示了它们的实用性，从而获得了二糖和三糖。
• A unique and rapid approach toward the efficient development of novel protein tyrosine phosphatase (PTP) inhibitors based on ‘clicked’ pseudo-glycopeptides
  作者：Jin-Wei Yang、Xiao-Peng He、Cui Li、Li-Xin Gao、Li Sheng、Juan Xie、Xiao-Xin Shi、Yun Tang、Jia Li、Guo-Rong Chen

  DOI：10.1016/j.bmcl.2010.12.126

  日期：2011.2

  binding affinity of the inhibitors with the targeted PTP. Docking simulation was eventually conducted to propose plausible binding modes of this compound series with PTP1B and CDC25B. Our approach readily realized from naturally abundant raw materials (sugar and amino acid) and via facile, regioselective and expeditious synthetic method (microwave-assisted click reaction) might provide new insights toward

  蛋白质酪氨酸磷酸酶（PTP）抑制剂的开发引起了人们的极大兴趣，因为许多PTP成员与主要的人类疾病（包括自身免疫性疾病，糖尿病和癌症）紧密相关。我们在这里报告了一种独特而快速的方法，用于开发基于三唑基假糖肽的新型PTP抑制剂实体。通过使用微波加速的Cu（I）催化的叠氮化物-炔烃1,3-偶极环加成反应（CuAAC或“点击反应”），一系列三唑连接的丝氨酰基，苏氨酸，苯丙氨酰基和酪氨酰基1- O-葡萄糖-或半乳糖苷仅在约30分钟内就可以高产率高效合成。连续的生物学分析鉴定出这些糖肽三唑是有利的PTP1B和CDC25B抑制剂，对TCPTP，LAR，SHP-1和SHP-2具有选择性。确定引入的氨基酸（Ser，Thr，Phe和Tyr）的结构多样性和单糖支架上的差向异构体（Glc或Gal）均会影响相应的抑制活性和选择性。此外，已证明苄基糖支架在增强抑制剂与靶向PTP的结合亲和力中起关键作用。最终进行了对接
• Study of metal and acid catalysed deprotection of propargyl ethers of alcohols via their allenyl ethers
  作者：Hari Babu Mereyala、Srinivas Reddy Gurrala、S Krishna Mohan

  DOI：10.1016/s0040-4020(99)00631-6

  日期：1999.9

  A new method for the deprotection of prop-2-ynyl ethers 1b-9b is described. Isomerisation of 1b-9b to O-allenyl ethers 1d-9d and deprotection by reaction with Hg(OCOCF3)(2), aq.HCl, aq.CF3CO2H and best by use of a catalytic amount of OsO4 is described to obtain the alcohols 1a-9a in good yield. Application of this method for the deprotection of prop-2-enyl ethers 7c,8c,10c-13c via their corresponding prop-1-enyl ethers 7e,8e,10e-13e to obtain the corresponding alcohols 7a,8a,10a-13a is also described, (C) 1999 Elsevier Science Ltd. All rights reserved.