Acetic acid (2R,3R,4S,5R,6R)-2,3-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4-diacetoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester | 81661-67-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-2,3-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4-diacetoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
• 英文别名: Gal2Ac3Ac(b1-4)a-Glc1Ac2Ac3Ac6Ac；[(2R,3R,4S,5R,6R)-4,5,6-triacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4-diacetyloxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 81661-67-8
• 化学式: C₂₄H₃₄O₁₇
• 分子量: 594.524
• InChiKey: JWXINSMWFMIRCL-NASJFSCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  226
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-2,3-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4-diacetoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 在 吡啶 、 calcium sulfate 、 4 A molecular sieve 、 silver perchlorate 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 135.0h， 生成 O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-O-(2,3-di-O-acetyl-6-O-benzoyl-β-D-galactopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-α-D-glucopyranose
  参考文献：
  名称：

  Forsman抗原的五糖链的合成。

  摘要：

  Forssman抗原O-（2-acetamido-2-deoxy-alpha-D-galactopyranosyl）-（1的五糖链导致3）-O-（2-acetamido-2-deoxy-beta-D-galactopyranosyl） -（1导致3）-O-α-D-吡喃半乳糖-（1导致4）-O-β-D-吡喃半乳糖-（1导致4）-D-吡喃葡萄糖（46）通过嵌段合成法合成其中两个D-半乳糖残基之间形成了α-D-糖苷键。三糖O-（6-O-乙酰基-2-叠氮基3,4-二-O-苯甲酰基-2-脱氧-α-D-吡喃半乳糖基）-（1导致3）-O-（6-O-乙酰-4-O-苄基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃半乳糖基）-（1导致3）-6-O-乙酰基-2,4-二-O-苄基-α-D-吡喃半乳糖基溴化物（40）（通过乙酰分解O-（6-O-乙酰基-2-叠氮基3，4-二-O-苯甲酰基-2-脱氧-α-D-吡喃半乳糖

  DOI：

  10.1016/s0008-6215(00)81032-0
• 作为产物：
  描述：

  Acetic acid (3R,4S,5R,6R)-2,3-diacetoxy-6-acetoxymethyl-5-[(4aR,6S,7R,8S,8aS)-7,8-diacetoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-4-yl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2,3-di-O-acetyl-β-D-glucopyranosyl-(1->4)-1,2,3,6-tetra-O-acetyl-β-D-glucopyranose 、 Acetic acid (2R,3R,4S,5R,6R)-2,3-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4-diacetoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Optimized design and synthesis of chemical dimerizer substrates for detection of glycosynthase activity via chemical complementation

  摘要：

  Glycosynthases catalyze the formation of a glycosidic bond between a glycosyl fluoride donor substrate and a glycosyl acceptor substrate with high yield, thus providing a valuable approach for the synthesis of carbohydrates and glycoconjugates. Chemical complementation can be used to link glycosynthase activity to the transcription of a reporter gene in vivo, providing a selection for the directed evolution of glycosynthase enzymes with improved properties. In this approach, glycosynthase activity is detected as covalent coupling between a small molecule disaccharide acceptor substrate and a small molecule disaccharide alpha-fluoro donor substrate. Here we report the optimized design and synthesis of these small molecule substrates. These optimized substrates are shown to give a robust, glycosynthase-dependent transcriptional read-out in the chemical complementation assay. The full synthesis and characterization of these substrates are reported for the first time. These optimized chemical dimerizer substrates should allow the potential of chemical complementation for the directed evolution of glycosynthases with diverse substrate specificities and improved properties to be fully realized. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.034

文献信息

• Facile Access to Novel [60]Fullerenyl Diethers and [60]Fullerene–Sugar Conjugates via Annulation of Diol Moieties
  作者：Wen-Qiang Zhai、Sheng-Peng Jiang、Ru-Fang Peng、Bo Jin、Guan-Wu Wang

  DOI：10.1021/acs.orglett.5b00536

  日期：2015.4.17

  A general and facile annulation of various diol motifs to [60]fullerene has been developed. This protocol can afford not only 6- to 10-membered-ring fullerenyl diethers in one step from simple acyclic diols but also directly couple [60]fullerene with a variety of structurally diverse sugars. The [60]fullerene-sugar conjugates formed do not require any linker moiety and maintain their inherent structural integrity. The electrochemistry of the fullerenyl diethers and [60]fullerene-sugar conjugates has also been investigated.