苄基 O-七乙酰基-beta-D-乳糖苷 | 67310-53-6

• 物质功能分类: 生物化工 - 糖类化合物 - 双糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苄基 O-七乙酰基-beta-D-乳糖苷
• 中文别名: 苄基O-七乙酰基-BETA-D-乳糖苷；苄基O-七乙酰基-beta-D-乳糖苷；苄基 O-七乙酰基-BETA-D-乳糖苷
• 英文名称: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(benzyloxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside；benzyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside；Benzyl 2,3,6,2',3',4',6'-Hepta-O-acetyl-β-lactoside；benzyl hepta-O-acetyl-β-lactoside；β-(1-benzyl)peracetyllactose；benzyl-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside]；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-phenylmethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 67310-53-6
• 化学式: C₃₃H₄₂O₁₈
• 分子量: 726.686
• InChiKey: BDMTWMBGISDBOQ-LZWHNZSHSA-N

物化性质

• 熔点：
  141-143°C
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  51
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

安全信息

• 储存条件：
  -20°C 冰箱

反应信息

• 作为反应物：
  描述：

  苄基 O-七乙酰基-beta-D-乳糖苷 在 15-冠醚-5 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 20.5h， 生成 benzyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of lacto- N -tetraose

  摘要：

  Human milk oligosaccharides (HMOs) are the third largest macromolecular component of breast milk and offer infants numerous health benefits, most of which stem from the development of a healthy microbiome. Characterization, quantification, and chemical derivatization of HMOs remains a frontier issue in glycobiology due to the challenge of isolating appreciable quantities of homogenous HMOs from breast milk. Herein, we report the synthesis of the human milk tetrasaccharide lacto-N-tetraose (LNT). LNT is ubiquitous in human breast milk as it is a core structure common to longer-chain HMOs and many glycolipids. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2017.02.001
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 氢溴酸 、 碘 、 溶剂黄146 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 苄基 O-七乙酰基-beta-D-乳糖苷
  参考文献：
  名称：

  Synthesis of lacto- N -tetraose

  摘要：

  Human milk oligosaccharides (HMOs) are the third largest macromolecular component of breast milk and offer infants numerous health benefits, most of which stem from the development of a healthy microbiome. Characterization, quantification, and chemical derivatization of HMOs remains a frontier issue in glycobiology due to the challenge of isolating appreciable quantities of homogenous HMOs from breast milk. Herein, we report the synthesis of the human milk tetrasaccharide lacto-N-tetraose (LNT). LNT is ubiquitous in human breast milk as it is a core structure common to longer-chain HMOs and many glycolipids. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2017.02.001

文献信息

• Chemoenzymatic Synthesis of a Library of Human Milk Oligosaccharides
  作者：Zhongying Xiao、Yuxi Guo、Yunpeng Liu、Lei Li、Qing Zhang、Liuqing Wen、Xuan Wang、Shukkoor Muhammed Kondengaden、Zhigang Wu、Jun Zhou、Xuefeng Cao、Xu Li、Cheng Ma、Peng George Wang

  DOI：10.1021/acs.joc.6b00478

  日期：2016.7.15

  decades. In this study, an efficient chemoenzymatic strategy, namely core synthesis/enzymatic extension (CSEE), for rapid production of diverse HMOs was reported. On the basis of 3 versatile building blocks, 3 core structures were chemically synthesized via consistent use of oligosaccharyl thioether and oligosaccharyl bromide as glycosylation donors in a convergent fragment coupling strategy. Each of these

  人乳寡糖（HMO）是人乳中作为主要成分之一存在的各种未结合的聚糖家族。由于HMO的多样性和复杂性，其表征，定量和生物功能研究仍然是一个巨大的挑战。同类HMO库的可访问性对于解决困扰学术界数十年的这些问题至关重要。在这项研究中，报告了一种有效的化学酶策略，即核心合成/酶延伸（CSEE），用于快速生产各种HMO。在3个通用构建基的基础上，通过在收敛片段偶联策略中一致使用寡糖基硫醚和寡糖溴化物作为糖基化供体，化学合成了3个核心结构。然后，这些核心结构中的每一个都通过4种健壮的糖基转移酶扩展至多达11个HMO。化学合成31种HMO的文库，并通过MS和NMR进行表征。CSEE确实提供了一种实用的方法来为各种应用收集结构明确的HMO。
• Trypanosoma cruzi trans-sialidase alternative substrates: Study of the effect of substitution in C-6 in benzyl β-lactoside
  作者：Pablo Morrone-Pozzuto、Maria Laura Uhrig、Rosalia Agusti

  DOI：10.1016/j.carres.2019.04.003

  日期：2019.5

  is a cell surface protein that participates in the adhesion and invasion mechanisms of the parasite into the host cells, making it an attractive target for inhibitors design. In order to contribute to the knowledge of the interaction between TcTS and their acceptor substrates, we designed and synthesized a library of 20 benzyl lactosides substituted in C-6 of the glucose residue with a series of 1,2

  克鲁氏锥虫转唾液酸酶（TcTS）是一种细胞表面蛋白，参与该寄生虫对宿主细胞的粘附和侵袭机制，使其成为抑制剂设计的诱人靶标。为了有助于了解TcTS及其受体底物之间的相互作用，我们设计并合成了一个库，该库由葡萄糖残基C-6中取代的20种苄基乳糖苷组成，这些1,2,3-三唑衍生物系列C-4位的芳族取代基。该文库是通过Cu（I）催化的炔-叠氮化物环加成反应（“点击化学”）在C-6位上被叠氮基官能化的苄基β-乳糖苷与一系列2-炔丙基苯基醚之间制备的。本文中，我们分析了三唑基-乳糖衍生物在高效阴离子交换色谱（HPAEC）上的色谱行为，以及它们作为TcTS受体和N-乙酰基乳糖胺唾液酸化抑制剂的活性。以优异的产率获得了三唑基衍生物，并且它们均表现为中等的替代性底物。庞大的疏水取代基的存在显着增加了HPAEC中的保留时间，但并未显着影响其对TcTS的受体性能。
• Total synthesis of globotriaosyl-E and Z-ceramides and isoglobotriaosyl-E-ceramide
  作者：Katsuya Koike、Mamoru Sugimoto、Susumu Sato、Yukishige Ito、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/0008-6215(87)80181-7

  日期：1987.6

  Stereoselective, total synthesis of O-alpha-D-galactopyranosyl-(1----4) -O-beta-D-galactopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----1)-N -tetracosanoyl-[2S,3R,4E (and 4Z)]-sphingenine and O-alpha-D -galactopyranosyl-(1----3)-O-beta-D-galactopyranosyl-(1----4)-O-beta-D -glucopyranosyl-(1----1)-N-tetracosanoyl-(2S,3R,4E)-sphin gen ine was achieved by using O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)

  O-α-D-吡喃半乳糖基-（1 ---- 4）-O-β-D-吡喃半乳糖基-（1 ---- 4）-O-β-D-吡喃葡萄糖基-（1-的立体选择性全合成--- 1）-N-十四烷酰基-[2S，3R，4E（和4Z）]-鞘氨醇和O-α-D-吡喃半乳糖基-（1 ---- 3）-O-β-D-吡喃半乳糖基-（通过使用O-（2,3）可实现1 ---- 4）-O-β-D-吡喃葡萄糖基-（1 ---- 1）-N-十四烷酰基-（2S，3R，4E）-斯宾碱，4,6-四-O-乙酰基-α-D-吡喃半乳糖基）-（1 ---- 4）-O-（2,3,6-三-O-乙酰基-β-D-吡喃半乳糖基）-（ 1 ---- 4）-2,3,6-三-O-乙酰基-α-D-吡喃葡萄糖基三氯乙酰亚氨酸酯，O-（2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基） -（1 ---- 4）-O-（2,3,6-三-O-乙酰基-β-D-吡喃半乳糖基）-（1
• 4-O-β-d-galactopyranosyl-3-O-methyl-d-glucose: A new synthesis and application to the evaluation of intestinal lactase
  作者：Alfonso Fernandez-Mayoralas、Manuel Martin-Lomas、Daniel Villanueva

  DOI：10.1016/0008-6215(85)85051-5

  日期：1985.7

  4-O-beta-D-Galactopyranosyl-3-O-methyl-D-glucose (1, 3-O-methyl-lactose) has been prepared from benzyl 2,6-di-O-benzyl-4-O-(2,6-di-O-benzyl-3, 4-O-isopropylidene-beta-D-galactopyranosyl)-beta-D-glucopyranoside (5) and from benzyl 2,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-beta-D-galactopyranosyl)-bet a-D-glucopyranoside (15). Partial benzylation of benzyl 3',4'-O-isopropylidene-beta-lactoside (4)

  由苄基2,6-二-O-苄基-4-O-（-）制备4-O-β-D-半乳糖吡喃糖基-3-O-甲基-D-葡萄糖（1，3-O-甲基-乳糖） 2,6-二-O-苄基-3，4-O-异亚丙基-β-D-吡喃半乳糖基）-β-D-吡喃吡喃糖苷（5）和2,6-二-O-苄基-4-O- （2,3,4,6-四-O-苄基-β-D-吡喃半乳糖基）-bet aD-吡喃葡萄糖苷（15）。苄基3'，4'-O-异亚丙基-β-乳糖苷（4）的部分苄基化得到5，苄基β-乳糖苷（13）或苄基七-O-乙酰基-β-乳糖苷（24）的部分苄基化得到15还分离并表征了来自4、13和24的部分苄基化的所有其他产物。肠内乳糖酶在体外水解1在20小时内是线性的；Vmax为乳糖的Vmax的5％，Km为120mM（乳糖为30mM）。
• Synthesis and biological evaluation of α-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3)
  作者：Chengfeng Xia、Qingjia Yao、Jens Schümann、Emmanuel Rossy、Wenlan Chen、Lizhi Zhu、Wenpeng Zhang、Gennaro De Libero、Peng George Wang

  DOI：10.1016/j.bmcl.2006.01.040

  日期：2006.4

  Glycoceramides call activate NKT cells by binding with CD1d to produce IFN-gamma, IL-4, and other cytokines. An efficient synthetic pathway for alpha-galactosylceramide (KRN7000) was established by coupling a protected galactose donor to a properly protected ceramide. During the investigation, it was discovered that when the ceramide was protected with benzyl groups, only beta-galactosylceramide was produced from the glycosylation reaction. In contrast, the ceramide with benzoyl protecting groups produced alpha-galactosylceramide. Isoglobotrihexosylceramide (iGb3) was prepared by glycosylation of Gal alpha 1-3Gal beta 1-4Glc donor with 2-azidosphingosine in high yield. Biological assays on the synthetic KRN7000 and iGb3 were performed using human and murine iNKT cell clones or hybridomas. (C) 2006 Elsevier Ltd. All rights reserved.