octyl (β-D-galactopyranosyl)-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranoside | 178977-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl (β-D-galactopyranosyl)-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: octyl 2-deoxy-2-acetamido-4-O-β-D-galactopyranosyl-β-D-glucopyranoside；Octyl 2-(Acetylamino)-2-deoxy-4-O-beta-D-galactopyranosyl-beta-D-glucopyranoside；N-[(2R,3R,4R,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-octoxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 178977-64-5
• 化学式: C₂₂H₄₁NO₁₁
• 分子量: 495.568
• InChiKey: ZMHROAVAQHSNOY-OEUZHLKXSA-N

物化性质

• 溶解度：
  soluble in No data available

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  octyl (β-D-galactopyranosyl)-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranoside 在 palladium dihydroxide 咪唑 、 sodium hydroxide 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 、 水 、 氢气 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 82.0h， 生成 sodium; 5-acetylamino-2-[2-(5-acetylamino-4-hydroxy-2-hydroxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-4-hydroxy-6-(1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylate
  参考文献：
  名称：

  Practical Synthesis of Sulfated Analogs of Lactosamine and Sialylated Lactosamine Derivatives

  摘要：

  A series Of beta-D-Gal-(1 --> 4)-beta-D-GlcNAc-octyl, NeuAcalpha-(2 --> 3)-beta-D-Gal-(1 --> 4)-beta-D-GlcNAc-octyl, and their 6-O-sulfated and 6'-O-sulfated analogs (1-6) were synthesized in a concise manner starting from readily accessible monosaccharide intermediates. The syntheses involved formation of an orthogonally protected disaccharide and a trisaccharide from which all six compounds were derived.

  DOI：

  10.1081/car-200030027
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 palladium on activated charcoal 甲醇 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 octyl (β-D-galactopyranosyl)-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient synthesis of 3′-glycosylated LacNAc-based oligosaccharides

  摘要：

  LacNAc-based oligosaccharides, including sialyl-(2 --> 3)-LacNAc, dimeric sialyl-(2 --> 3) -LacNAc, trimeric sialyl-(2 --> 3)-LacNAc, beta-glucuronyl-(1 --> 3)-LacNAc, and 3-sulfo-beta-glucuronyl-(1 --> 3)-LacNAc, were synthesized efficiently from a single protected LacNAc derivative having both OH-3' and 4' unprotected. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00332-1

文献信息

• Fluoridolysis of 5,6-epoxy carbohydrates: application to the synthesis of 5-fluoro lactosamine and isolactosamine glycosides
  作者：Tara L. Hagena、James K. Coward

  DOI：10.1016/j.tetasy.2009.03.025

  日期：2009.5

  The synthesis of 6-selenophenyl derivatives of β-1,3 and β-1,4 disaccharides has been explored for the purpose of extending our epoxide fluoridolysis methodology to the synthesis of 5-fluoro analogues of N-acetyl isolactosamine (isoLacNAc, lacto-N-biose) and N-acetyl lactosamine (LacNAc) glycosides. Successful synthesis of the C-6 selenium-containing disaccharides was achieved via Lewis acid-mediated

  为了将我们的环氧化物荧光分解方法扩展到N-乙酰基异乳糖胺（isoLacNAc，乳酸酯-）的5-氟类似物的合成，已经探索了β-1,3和β-1,4二糖的6-硒苯基衍生物的合成。N-二糖）和N-乙酰基乳糖胺（LacNAc）糖苷。通过路易斯酸介导的供体和受体底物成功合成了含C-6硒的二糖，后者含有选择性保护的C-6羟基，可最终转化为所需的6-硒代苯二糖。相反，在多种条件下使用含硒受体底物不能产生所需的含硒二糖。将6-硒代苯衍生物氧化为相应的亚硒酸盐，然后进行热消除，得到环外烯烃，其被转化为5，6-环氧化物。环氧氟化反应产生所需的目标化合物，即1型和2型聚糖的5-氟β-辛基糖苷类似物。
• Synthesis of Oligosaccharides Designed to form Micelles, Corresponding to Structures Found in Ovarian Cyst Fluid
  作者：Therese Buskas、Peter Konradsson

  DOI：10.1080/07328300008544063

  日期：2000.1

  The syntheses of alpha-D-GlcpNAc-(1-->4)-beta-D-Galp-(1-->4)-beta-D-GlcNAc-(1-->O)-(CH2)(15)CH3 (1) and fragments thereof, corresponding to structures found in human ovarian cyst fluid, are described. Silver triflate promoted coupling of 3.4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranosyl bromide (12) and galactose acceptor (11) gave a disaccharide donor (13), which was readily transformed into the corresponding bromo-derivative 18. For the synthesis of disaccharide beta-D-Galp-(1-->4)-D-GlcNAc, several differently protected glucosamine accepters were prepared. It was found that cetyl alcohol needed to be introduced after the formation of the P-galactoside bond. Glycosylation of pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (30) with (3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-alpha-D-galactopyranosyl bromide (18) by use of silver triflate as promoter gave the desired trisaccharide 31. Finally 31 was transformed via coupling to the long alkyl chain aglycon and deprotection into the title compound 1.
• Synthesis of lactosamine derivatives using β-d-galactosidase from Bacillus circulans
  作者：Shuichi Takayama、Makoto Shimazaki、Lei Qiao、Chi-Huey Wong

  DOI：10.1016/0960-894x(96)00184-9

  日期：1996.5

  Various lactosamine derivatives that are versatile building blocks for oligosaccharide synthesis were obtained with excellent regioselectivity and moderate to high yields using beta-D-galactosidase from Bacillus circulans as the biocatalyst. (C) 1996 Elsevier Science Ltd
• Efficient synthesis of 3′-glycosylated LacNAc-based oligosaccharides
  作者：Yili Ding、Minrou Fukuda、Ole Hindsgaul

  DOI：10.1016/s0960-894x(98)00332-1

  日期：1998.7

  LacNAc-based oligosaccharides, including sialyl-(2 --> 3)-LacNAc, dimeric sialyl-(2 --> 3) -LacNAc, trimeric sialyl-(2 --> 3)-LacNAc, beta-glucuronyl-(1 --> 3)-LacNAc, and 3-sulfo-beta-glucuronyl-(1 --> 3)-LacNAc, were synthesized efficiently from a single protected LacNAc derivative having both OH-3' and 4' unprotected. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Practical Synthesis of Sulfated Analogs of Lactosamine and Sialylated Lactosamine Derivatives
  作者：Anup Kumar Misra、Geetanjali Agnihotri、Soni Kamlesh Madhusudan、Pallavi Tiwari

  DOI：10.1081/car-200030027

  日期：2004.12.29

  A series Of beta-D-Gal-(1 --> 4)-beta-D-GlcNAc-octyl, NeuAcalpha-(2 --> 3)-beta-D-Gal-(1 --> 4)-beta-D-GlcNAc-octyl, and their 6-O-sulfated and 6'-O-sulfated analogs (1-6) were synthesized in a concise manner starting from readily accessible monosaccharide intermediates. The syntheses involved formation of an orthogonally protected disaccharide and a trisaccharide from which all six compounds were derived.