Methyl O-α-D-galactopyranosyl-(1->3)-β-D-galactopyranoside | 18449-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl O-α-D-galactopyranosyl-(1->3)-β-D-galactopyranoside
• 英文别名: methyl α-D-galactopyranosyl-(1->3)-β-D-galactopyranoside；methyl 3-O-α-D-galactopyranosyl-β-D-galactopyranoside；α-Galp-(1->3)-β-Galp-OMe；(2R,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 18449-79-1
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: WOKXHOIRHHAHDA-HKTRSZBRSA-N

物化性质

• 沸点：
  669.2±55.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以70%的产率得到Methyl O-α-D-galactopyranosyl-(1->3)-β-D-galactopyranoside
  参考文献：
  名称：

  2,3,4,6-四-O-苄基-β-D-吡喃半乳糖基苯基亚砜作为糖基供体。合成一些含有α-D-吡喃半乳糖基的寡糖。

  摘要：

  DOI：

  10.1016/s0008-6215(00)90937-6

文献信息

• Preparation of α and β anomers of various isomeric methyl O-d-galactopyranosyl-d-galactopyranosides. Standards for interpretation of 13C-n.m.r. spectra of d-galactopyranans
  作者：Philip A.J. Gorin

  DOI：10.1016/s0008-6215(00)80790-9

  日期：1982.2

  r. resonances of α and β anomers of methyl O - d -galactopyranosyl-β- d -galactopyranosides. In terms of application of these shift values and those of related d -galactobioses to the structural analysis of d -galactopyranans by shift comparisons, some generalizations can be made. For β- d -galactopyranans, the resonances of glycosyloxylated carbon atoms of methyl O -β- d -galactopyranosyl-β- d -galactopyranosides

  摘要通过将2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物与适当的部分O-缩合制备甲基O-β-d-吡喃半乳糖基-β-d-吡喃半乳糖苷的四个异构体。甲基β-d-吡喃半乳糖苷的取代衍生物。在溴化汞的存在下，3,4,6-三-O-乙酰基-1,2-O-（1-乙氧基亚乙基）-α-d-吡喃半乳糖与相同的受体反应导致形成α和β β键。因此，有可能分配13个Cn.mr共振的甲基O-d-吡喃半乳糖苷-β-d-吡喃半乳糖苷的α和β端基异构体。在通过移位比较将这些移位值和相关的d-半乳双歧杆菌的值应用于d-半乳糖吡喃聚糖的结构分析方面，可以做出一些概括。对于β-d-吡喃半乳糖，甲基O-β-d-吡喃半乳糖苷-β-d-吡喃半乳糖苷的糖基氧基化碳原子的共振对结构敏感，并且似乎具有典型值，而随着C-1'信号的移位观察到有限的变化。另一方面，为了将结构分配给含有α键的d-吡喃半乳糖，甲基O-α-d-吡喃半乳糖基-
• A simple strategy for changing the regioselectivity of glycosidase-catalysed formation of disaccharides
  作者：Kurt G.I. Nilsson

  DOI：10.1016/0008-6215(87)80271-9

  日期：1987.9

  The regioselectivity of glycosidase-catalysed formation of disaccharides can be changed by using alpha- or beta-glycosyl acceptors with various aglycons. The preponderant formation of other than (1----6) linkages can be effected with glycosidases which normally give (1----6) linkages. Thus, an alpha-D-galactosidase can be induced to catalyse the formation mainly of alpha-(1----2)-, alpha-(1----3),

  通过使用带有各种糖苷配基的α-或β-糖基受体可以改变糖苷酶催化的二糖形成的区域选择性。除了（1 ---- 6）键以外，优势糖的形成可以通过通常具有（1 ---- 6）键的糖苷酶来实现。因此，可以诱导α-D-半乳糖苷酶主要催化α-（1 ---- 2）-，α-（1 ---- 3）或α-（1 ---- 6）的形成。 ）连接的半乳​​糖苷。糖苷配基的结构和糖苷键的构型均可对二糖形成的区域选择性产生显着影响。描述了α-D-Galp-（1 ---- 3）-α-D-Galp-OMe，β-D-Galp-（1 ---- 3）的酶促合成，产率为20-30％ β-D-Galp-OMe，β-D-Galp-（1 ---- 6）-α-D-Galp-OMe，α-D-Manp-（1 ---- 2）-alpha- D-Manp-OMe，alpha-D-Manp-（1 ---- 6）-alpha-D-Manp-OMe，alpha-D-Galp-（1
• Glycosidase-catalysed synthesis of α-galactosyl epitopes important in xenotransplantation and toxin binding using the α-galactosidase from Penicillium multicolor
  作者：Suddham Singh、Michaela Scigelova、David H. G. Crout

  DOI：10.1039/a906020k

  日期：——

  The α-galactosidase from Penicillium multicolor catalyses highly regioselective galactosyl transfer on to mono- and di-saccharide acceptors that have a non-reducing terminal galactose unit to give products containing the α-D-Galp-(1→3)-D-Galp epitope found on pig tissue and which is responsible for the hyperacute rejection response in xenotransplantation of pig organs into man.

  多色青霉菌中的β-半乳糖苷酶催化具有非还原性末端半乳糖单元的单糖和二糖受体上的高度位点选择性半乳糖基转移，生成含有猪组织上发现的β-D-Galp-(1→3)-D-Galp表位的产物，该表位是猪器官异种移植到人体时产生超急性排斥反应的原因。
• Synthesis of α-Gal epitope derivatives with a galactosyltransferase–epimerase fusion enzyme
  作者：Jianwen Fang、Xi Chen、Wei Zhang、Adam Janczuk、Peng George Wang

  DOI：10.1016/s0008-6215(00)00245-7

  日期：2000.12

  beta -Gal epitopes are carbohydrate structures bearing an alpha -D-Galp-(1 --> 3)-beta -D-Galp terminus and are the main cause of antibody-mediated hyperacute rejection in xenotransplantation. Nine monosaccharides and ten disaccharides were evaluated as substrates for a fusion protein, which contains both alpha-(1 --> 3)-galactosyltransferase and uridine-5'-diphosphogalactose 4-epimerase. Four disaccharide and six trisaccharide alpha -Gal epitope derivatives were synthesized utilizing this novel fusion enzyme. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 2,3,4,6-Tetra-O-benzyl-β-d-galactopyranosyl phenyl sulfoxide as a glycosyl donor. Synthesis of some oligosaccharides containing and α-d-galactopyranosyl group
  作者：Arun K. Sarkar、Khushi L. Matta

  DOI：10.1016/s0008-6215(00)90937-6

  日期：1992.9