| 143729-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文别名: D-galβ(1-3)glucal；D-lactal；(2R,3R,4S,5R,6R)-2-[[(2R,3S,4R)-3-hydroxy-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-4-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 143729-05-9
• 化学式: C₁₂H₂₀O₉
• 分子量: 308.285
• InChiKey: KYNBCCXJVUMTDD-WCYSPJDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  、 alkaline earth salt of/the/ methylsulfuric acid 在 α(2-3)sialyl 30U transferase 、 calf intestine alkaline phosphatase 作用下， 以 水 为溶剂， 反应 144.0h， 以92%的产率得到5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid-(2-3)-O-β-D-galactopyranosyl-(1-3)-glucal
  参考文献：
  名称：

  Substrate specificity of fucosyl transferase III: An efficient synthesis of sialyl Lewis^x-, sialyl Lewis^a-derivatives and mimetics thereof

  摘要：

  Fucosyl转移酶III（FucT III）以其能够催化将岩藻糖转移到Galβ（1-3）GlcNAc和Galβ（1-4）GlcNAc的能力而被认定为FucT家族中最普遍的酶。为了探索FucT III在酶合成唾液酸Lewis x和唾液酸Lewis a衍生物方面的合成潜力，通过使用多种天然底物类似物探测其底物特异性。当N-乙酰葡萄糖胺被D-葡糖醛，（R，R）-1,2-环己二醇和（R，R）-丁烷-2,3-二醇替代时，发现了一系列可接受的底物。尽管与天然底物的反应速率较低，但它们被证明足以合成大量的制备量。关键词：fucosyl转移酶III，唾液酸Lewis a，唾液酸Lewis x，碳水化合物类似物。

  DOI：

  10.1139/v00-081
• 作为产物：
  描述：

  [(2R,3S,4R)-3-acetyloxy-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以97%的产率得到
  参考文献：
  名称：

  A combined chemical and enzymatic strategy for the construction of carbohydrate-containing antigen core units

  摘要：

  Glycosidase-mediated coupling of glycal acceptors with galactose donors affords beta1,3-linked disaccharides that are versatile intermediates for further chemical and enzymatic manipulation. The utility of these disaccharides is demonstrated by the elaboration of these compounds into the type I and type IV core disaccharides of carbohydrate-containing antigens. Further conversion of the type IV disaccharide to a mucin-type trisaccharide (Galbeta1,3(GlcNAcbeta1,6)GalNAc) was accomplished with the use of a beta1,6-N-acetylglucosaminyltransferase. This combined use of enzymatic and chemical methodologies allows for the rapid assembly, with high regio- and stereoselectivity, of core oligosaccharides of biologically important glycoconjugates.

  DOI：

  10.1021/jo00068a030

文献信息

• Chloroperoxidase-catalyzed asymmetric synthesis: enantioselective reactions of chiral hydroperoxides with sulfides and bromohydroxylation of glycals
  作者：Hong Fu、Hirosato Kondo、Yoshitaka Ichikawa、Gary C. Look、Chi Huey Wong

  DOI：10.1021/jo00052a048

  日期：1992.12

  This paper describes the use of chloroperoxidase (CPO) from Caldanomyces fumago in the oxidation of sulfides to prepare (R)-sulfoxides with excellent ee (97-100%) and yield (66-92%) using H2O2 as oxidant. When racemic 1-phenylethyl hydroperoxides were used in the oxidation of sulfides, the corresponding (R)-alcohol generated from the oxidant and the unreacted (S)-hydroperoxide were recovered with high enantiomeric purity. The enantioselectivity in the enzymatic asymmetric oxidation was found to depend on the concentrations of the substrate and enzyme. Chloroperoxidase was also used in the regioselective bromohydration of certain saccharide glycals with KBr and H2O2 to give the corresponding 2-deoxy-2-bromo saccharides.
• Azaglycosylation of complex stannyl alkoxides with glycal-derived iodo sulfonamides: a straightforward synthesis of sialyl-Lewis X antigen and other oligosaccharide domains
  作者：Samuel J. Danishefsky、Koshi Koseki、David A. Griffith、Jacquelyn Gervay、John M. Peterson、Frank E. McDonald、Takeshi Oriyama

  DOI：10.1021/ja00047a078

  日期：1992.10
• Enzymatic syntheses and selective hydrolysis of O-β-d-galactopyranosides using a marine mollusc β-galactosidase
  作者：Assunta Giordano、Annabella Tramice、Giuseppina Andreotti、Ernesto Mollo、Antonio Trincone

  DOI：10.1016/j.bmcl.2004.10.016

  日期：2005.1

  The use of crude extract of the hepatopancreas of Aplysia fasciata, a large mollusc belonging to the order Anaspidea containing a beta-galactosidase activity, was reported for the synthesis of different galactosides. Good yields with polar acceptors and the uncommon beta-1-3 selectivity in the transgalactosylation reactions with most of the acceptors were observed. A beta-1-2 selectivity in the hydrolytic conditions was also observed and discussed. (C) 2004 Elsevier Ltd. All rights reserved.