3,4-Di-O-acetyl-1,5-anhydro-2-deoxy-D-threo-pentitol | 78870-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 3,4-Di-O-acetyl-1,5-anhydro-2-deoxy-D-threo-pentitol
• 英文别名: 1,5-anhydro-2-deoxy-3,4-di-O-acetyl-α-D-xylitol；di-O-acetyl-D_g-threo-1,5-anhydro-2-deoxy-pentitol；trans-3,4-Diacetoxy-tetrahydro-pyran；Di-O-acetyl-D_g-threo-1,5-anhydro-2-desoxy-pentit；(3R,4R)-diacetoxytetrahydropyran；[(3R,4R)-3-acetyloxyoxan-4-yl] acetate
• CAS: 78870-53-8
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: GWMTXNVTJAKAIO-RKDXNWHRSA-N

物化性质

• 沸点：
  261.4±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-Di-O-acetyl-1,5-anhydro-2-deoxy-D-threo-pentitol 在 4-二甲氨基吡啶 、 sodium methylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.5h， 生成
  参考文献：
  名称：

  Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors

  摘要：

  Lysophosphatidylserine (LysoPS), an endogenous ligand of G protein-coupled receptors, consists of L-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages, respectively. An ester linkage of phosphatidylserine can be hydrolyzed at the 1-position or at the 2-position to give 2-acyl lysophospholipid or 1-acyl lysophospholipid, respectively. 2-Acyl lysophospholipid is in nonenzymatic equilibrium with 1-acyl lysophospholipid in vivo. On the other hand, 3-acyl lysophospholipid is not found, at least in mammals, raising the question of whether the reason for this might be that the 3-acyl isomer lacks the biological activities of the other isomers. Here, to test this idea, we designed and synthesized a series of new 3-acyl lysophospholipids. Structure- activity relationship studies of more than 100 "glycol surrogate" derivatives led to the identification of potent and selective agonists for LysoPS receptors GPR34 and P2Y10. Thus, the non-natural 3-acyl compounds are indeed active and appear to be biologically orthogonal with respect to the physiologically relevant 1- and 2-acyl lysophospholipids.

  DOI：

  10.1021/acs.jmedchem.0c01126
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-D-xylopyranosyl bromide 在 palladium on activated charcoal 、 氢气 、 sodium acetate 、 copper(II) acetate monohydrate 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 11.0h， 生成 3,4-Di-O-acetyl-1,5-anhydro-2-deoxy-D-threo-pentitol
  参考文献：
  名称：

  Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors

  摘要：

  Lysophosphatidylserine (LysoPS), an endogenous ligand of G protein-coupled receptors, consists of L-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages, respectively. An ester linkage of phosphatidylserine can be hydrolyzed at the 1-position or at the 2-position to give 2-acyl lysophospholipid or 1-acyl lysophospholipid, respectively. 2-Acyl lysophospholipid is in nonenzymatic equilibrium with 1-acyl lysophospholipid in vivo. On the other hand, 3-acyl lysophospholipid is not found, at least in mammals, raising the question of whether the reason for this might be that the 3-acyl isomer lacks the biological activities of the other isomers. Here, to test this idea, we designed and synthesized a series of new 3-acyl lysophospholipids. Structure- activity relationship studies of more than 100 "glycol surrogate" derivatives led to the identification of potent and selective agonists for LysoPS receptors GPR34 and P2Y10. Thus, the non-natural 3-acyl compounds are indeed active and appear to be biologically orthogonal with respect to the physiologically relevant 1- and 2-acyl lysophospholipids.

  DOI：

  10.1021/acs.jmedchem.0c01126

文献信息

• Highly α- and β-Selective Radical<i> C</i>-Glycosylation Reactions Using a Controlling Anomeric Effect Based on the Conformational Restriction Strategy. A Study on the Conformation−Anomeric Effect− Stereoselectivity Relationship in Anomeric Radical Reactions
  作者：Hiroshi Abe、Satoshi Shuto、Akira Matsuda

  DOI：10.1021/ja011321t

  日期：2001.12.1

  stereoselectivity of anomeric radical reactions was significantly influenced by the anomeric effect, which can be controlled by restricting the conformation of the radical intermediate, the proper conformational restriction of the pyranose ring of the substrates would therefore make highly alpha- and beta-stereoselective anomeric radical reactions possible. Thus, the conformationally restricted 1-phenylseleno-D-xylose

  我们假设，由于异头自由基反应的立体选择性受到异头效应的显着影响，这可以通过限制自由基中间体的构象来控制，因此对底物吡喃糖环的适当构象限制将使高度α-和β-立体选择性异头自由基反应是可能的。因此，设计了构象受限的 1-苯基硒-D-木糖衍生物 9 和 10，受限于 (4)C(1)-构象，以及受限于 (1)C(4)-构象的 11 和 12并通过在吡喃糖环上的羟基上引入适当的保护基团作为异头自由基反应的模型底物合成。Bu(3)SnD 的自由基氘化和 Bu(3)SnCH(2)CH [双键] CH(2) 或 CH(2) [双键] CHCN 的 C-糖基化，使用 (4)C( 1)-限制性底物 9 和 10，高度立体选择性地提供相应的 α-产物 (α/β = 97:3-85:15)，而 (1)C(4)-限制性底物 11 和 12 选择性地产生β - 产品（alpha/beta = 1:99-0:100）。
• Aspects of stereochemistry—I
  作者：J.S. Brimacombe、A.B. Foster、M. Stacey、D.H. Whiffen

  DOI：10.1016/0040-4020(58)80056-3

  日期：1958.1

  stabilities can be affected by hydrogen bonding from a substituent hydroxyl group to a ring oxygen. Additional evidence is provided in the case of the tetrahydropyran diols by [M]D values. The rate of reaction of the vicinal diols of these cyclic systems with glycol splitting reagents, and their zone electrophoretic mobility in an alkaline borate buffer is influenced by the presence of a ring oxygen.

  分子内氢键的如通过羟基拉伸区域红外光谱，在某些邻二醇确定的范围内，环己烷，环戊烷，四氢吡喃和四氢呋喃和相关化合物提供了用于不同的构象的稳定性的证据。在某些化合物中，这些稳定性可能会受到取代基羟基与环氧之间氢键的影响。对于四氢吡喃二醇，通过[ M ] D值提供了其他证据。这些环状体系的邻位二醇与二醇拆分剂的反应速率及其在碱性硼酸盐缓冲液中的区带电泳迁移率受环氧的影响。
• Methods and compositions for making antibodies and antibody derivatives with reduced core fucosylation
  申请人：SEATTLE GENETICS, INC.

  公开号：US10443035B2

  公开（公告）日：2019-10-15

  The invention provides methods and compositions for preparing antibodies and antibody derivatives with reduced core fucosylation.

  本发明提供了制备核心岩藻糖基化减少的抗体和抗体衍生物的方法和组合物。
• Olsen, Acta Chemica Scandinavica (1947), 1951, vol. 5, p. 1326,1334
  作者：Olsen

  DOI：——

  日期：——
• Identifying Specific Conformations by Using a Carbohydrate Scaffold: Discovery of Subtype-Selective LPA-Receptor Agonists and an Antagonist
  作者：Yoko Tamaruya、Masato Suzuki、Goshu Kamura、Motomu Kanai、Kotaro Hama、Kumiko Shimizu、Junken Aoki、Hiroyuki Arai、Masakatsu Shibasaki

  DOI：10.1002/anie.200454065

  日期：2004.5.17