methyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-α-D-glucopyranoside | 85193-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-α-D-glucopyranoside
• 英文别名: methyl 2-(acetylamino)-2-deoxy-4-O-beta-D-galactopyranosyl-alpha-D-glucopyranoside；N-[(2S,3R,4R,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-methoxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 85193-95-9
• 化学式: C₁₅H₂₇NO₁₁
• 分子量: 397.379
• InChiKey: PKPZITUQXLANSE-ZSCXKYTFSA-N

物化性质

• 沸点：
  752.2±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-α-D-glucopyranoside 在 二正丁基氧化锡 、 三氧化硫-三乙胺复合物 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 49.5h， 以53%的产率得到methyl 2-acetamido-2-deoxy-4-O-(3'-O-sulfo-β-D-galactopyranosyl)-α-D-glucopyranoside sodium salt
  参考文献：
  名称：

  In vitro sulfation of N-acetyllactosaminide by soluble recombinant human β-Gal-3′-sulfotransferase

  摘要：

  Membrane-bound beta-Gal-3'-sulfotransferase (GP3ST) was expressed and used for in vitro sulfation of Tamm-Horsfall glycoprotein. Further, the regioselective transfer of sulfate to an N-acetyllactosamine derivative could be realised with soluble chimeric GMT, also in combination with Lac transglycosylation by means of beta-galactosidase. Two alternative straightforward chemical syntheses for the target compound could be elaborated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.006
• 作为产物：
  描述：

  methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-α-D-glucopyranoside
  参考文献：
  名称：

  In vitro sulfation of N-acetyllactosaminide by soluble recombinant human β-Gal-3′-sulfotransferase

  摘要：

  Membrane-bound beta-Gal-3'-sulfotransferase (GP3ST) was expressed and used for in vitro sulfation of Tamm-Horsfall glycoprotein. Further, the regioselective transfer of sulfate to an N-acetyllactosamine derivative could be realised with soluble chimeric GMT, also in combination with Lac transglycosylation by means of beta-galactosidase. Two alternative straightforward chemical syntheses for the target compound could be elaborated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.006

文献信息

• Synthesis of di-, tri-, and tetra-saccharides corresponding to receptor structures recognised by Streptococcus pneumoniae
  作者：Jan Dahmén、Gösta Gnosspelius、Ann-Charlott Larsson、Thomas Lave、Ghazi Noori、Karin P»lsson、Torbjörn Frejd、Göran Magnusson

  DOI：10.1016/0008-6215(85)85219-8

  日期：1985.4

  Syntheses are described for methyl 2-acetamido-2-deoxy-4- O -β- d -galactopyranosyl-α- d -glucopyranoside, methyl 2-acetamido-2-deoxy-4- O -β- d -galactopyranosyl-β- d -glucopyranoside, methyl 3- O -(2-acetamido-2-deoxy-β- d -glucopyranosyl-β- d -galactopyranoside, methyl 3- O -(2-acetamido-2-deoxy-4- O -β- d -galactopyranosyl-β- d -glucopyranosyl)-β- d -galactopyranoside, and methyl 4- O -[3- O -(2-acetamido-2-deoxy-4-

  摘要描述了甲基2-乙酰氨基-2-脱氧-4-O-β-d-吡喃半乳糖苷-α-d-吡喃葡萄糖苷，甲基2-乙酰氨基-2-脱氧-4- O-β-d-吡喃半乳糖苷-β的合成-d-吡喃葡萄糖苷，甲基3- O-（2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖基-β-d-吡喃半乳糖苷，甲基3- O-（2-乙酰氨基-2-脱氧-4- O-β -d-吡喃半乳糖基-β-d-吡喃吡喃糖基）-β-d-吡喃半乳糖苷和甲基4-O-[3-O-（2-乙酰氨基-2-脱氧-4-O-β-d-吡喃半乳糖基-β- d-吡喃葡萄糖基）-β-d-吡喃半乳糖基]-β-d-吡喃葡糖苷。
• Synthesis of p-nitrophenyl 2-acetamido-2-deoxy-4-O-β-d-galactopyranosyl- β-d-glucopyranoside, and p-nitrophenyl 6-O-(2-acetamido-2-deoxy-3-O- and -4-O-β-d-galactopyranosyl- β-d-glucopyranosyl)-α-d-mannopyranoside
  作者：Surjit S. Rana、Joseph J. Barlow、Khushi L. Matta

  DOI：10.1016/0008-6215(83)88241-x

  日期：1983.3

  2-methyl-[4,6-di- O -acetyl-2-deoxy-3- O -(2,3,4,6-tetra- O - acetyl-β- d -galactopyranosyl)-α- d -glucopyrano]-[2,1- d ]-2-oxazoline proceeded readily, to give the protected trisaccharide derivative which, on deacetonation, followed by O -deacetylation, produced one of the title trisaccharides, namely, p -nitrophenyl 6- O -(2-acetamido-2-deoxy-3- O -β- d -galactopyranosyl-β- d -glucopyranosyl)-α- d -mannopyranoside

  摘要通过对2-乙酰氨基-3,6-反应生成的产物进行皂化反应，可轻松合成对硝基苯基2-乙酰氨基-2-脱氧-4-O-β-d-吡喃半乳糖基-β-d-吡喃葡萄糖苷。二-O-乙酰基-2-脱氧-4-O-（2,3,4,6-四-O-乙酰基-β-d-吡喃并吡喃糖基）-α-d-吡喃葡萄糖基氯和Amberlyst A-26对硝基苯酚。对硝基苯基2,3-O-异亚丙基-α-d-甘露吡喃糖苷（7）与易于获得的2-甲基-[4,6-二-O-乙酰基-2-脱氧-3-O-（ 2,3,4,6-四-O-乙酰基-β-d-吡喃并吡喃糖基）-α-d-吡喃吡喃基]-[2,1-d] -2-恶唑啉容易进行，得到被保护的三糖衍生物，脱乙酰化后，再经O-脱乙酰化，可产生标题三糖之一，即 对硝基苯基6-O-（2-乙酰氨基-2-脱氧-3-O-β-d-吡喃半乳糖基-β-d-吡喃葡萄糖基）-α-d-甘露吡喃糖苷。其他三糖，对硝基苯基6-O-（2-乙酰氨基
• Synthesis of novel disaccharides based on glycosyltransferases: β1,4galactosyltransferase
  作者：Chi-Huey Wong、Thomas Krach、Christine Gautheron-Le Narvor、Yoshitaka Ichikawa、Gary C. Look、Federico Gaeta、David Thompson、K.C. Nicolaou

  DOI：10.1016/s0040-4039(00)93482-8

  日期：1991.9

  Beta-1,4Galactosyltransferase and beta-galactosidase have been investigated with regard to their acceptor specificity and used in the synthesis of galactosides using 5-thioglucose, deoxyazaglucose, glucal, modified N-acetylglucosamine and glucose derivatives as acceptors.
• Disaccharide-derived 2-oxo- and 2-oximinoglycosyl bromides: novel, conveniently accessible building blocks for the expedient construction of oligosaccharides with .alpha.-D-glucosamine, .beta.-D-mannose, and .beta.-D-mannosamine as constituent sugars
  作者：Frieder W. Lichtenthaler、Eisuke Kaji、Sabine Weprek

  DOI：10.1021/jo00219a017

  日期：1985.9
• In vitro sulfation of N-acetyllactosaminide by soluble recombinant human β-Gal-3′-sulfotransferase
  作者：P. Greimel、Sabrina Jabs、Stefan Storch、Slim Cherif、Koichi Honke、Thomas Braulke、Joachim Thiem

  DOI：10.1016/j.carres.2006.02.006

  日期：2006.5

  Membrane-bound beta-Gal-3'-sulfotransferase (GP3ST) was expressed and used for in vitro sulfation of Tamm-Horsfall glycoprotein. Further, the regioselective transfer of sulfate to an N-acetyllactosamine derivative could be realised with soluble chimeric GMT, also in combination with Lac transglycosylation by means of beta-galactosidase. Two alternative straightforward chemical syntheses for the target compound could be elaborated. (c) 2006 Elsevier Ltd. All rights reserved.