4-O-β-D-galactopyranosyl-(1->4)-1,5-dideoxy-1,5-imino-D-glucitol | 134780-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-β-D-galactopyranosyl-(1->4)-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: 4-(-D-galactopyranosyl)-1-deoxynojirimycin；1-deoxy-4-O-β-D-galactopyranosyl-D-nojirimycin；(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-4,5-dihydroxy-2-(hydroxymethyl)piperidin-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 134780-11-3
• 化学式: C₁₂H₂₃NO₉
• 分子量: 325.316
• InChiKey: GNVIYGFSOIHFHK-AUCXZHPRSA-N

物化性质

• 沸点：
  628.4±55.0 °C(predicted)
• 密度：
  1.65±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  172
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-O-β-D-galactopyranosyl-(1->4)-1,5-dideoxy-1,5-imino-D-glucitol 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 吡啶 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 benzyl (2R,3R,4R,5S)-3-[[(3aS,4R,6R,7R,7aS)-7-benzoyloxy-4-(benzoyloxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-5-benzoyloxy-2-(benzoyloxymethyl)-4-hydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  An Efficient Synthesis of Sulfo Lewis X Analog Containing 1-Deoxynojirimycin

  摘要：

  Sulfo Lewis(x) analog containing 1-deoxynojirimycin (13) has been efficiently synthesized. Glycosidation of ethyl 2,3,4-tri-0-benzyl-1-thio-beta-D-fucopyranoside (5) with O-(2,6-di-O-benzoyl-3,4-isopropylidene-beta-D-galactopyranosyl)-(1-->4)-2, 6-di-O-benzoyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (4), prepared from O-beta-D-galactopyranosyl-(1-->4)-1,5-dideoxy-1, 5-imino-D-glucitol (1) via 3 steps, and subsequent acid hydrolysis of the isopropylidene group gave the desired trisaccharide diol derivative (7) in good yield. Compound 7 was easily converted into 3'-O-sulfo Lewis(x) analog (13) via 6 steps in high yield.

  DOI：

  10.1080/07328309808002348
• 作为产物：
  描述：

  Lactose 在 盐酸 、 N-碘代丁二酰亚胺 、 lithium aluminium tetrahydride 、 草酰氯 、 palladium on activated charcoal 、 三氟化硼乙醚 、 氢气 、 甲酸铵 、 sodium methylate 、 sodium acetate 、 sodium hydride 、 sodium cyanoborohydride 、 二甲基亚砜 、 sodium sulfate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~20.0 ℃ 、400.01 kPa 条件下， 反应 4.0h， 生成 4-O-β-D-galactopyranosyl-(1->4)-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  从天然和合成二糖开始合成糖基化 1-脱氧野尻霉素

  摘要：

  亚氨基糖是一类重要的天然产物，在有机合成、生物有机化学和药物化学方面得到了广泛的研究，但这些研究中只有少数是关于糖基化亚氨基糖的。在这里，提出了基于氧化还原胺化方案的糖基化 1-脱氧野尻霉素衍生物的一般合成路线，该方案在过去也被证明是合成 1-脱氧野尻霉素的通用途径。该策略可应用于商业二糖，如四个示例所示，也可应用于非市售二糖，并为此目的合成，如第五个示例所示。

  DOI：

  10.1002/ejoc.201801461

文献信息

• Glycosyltransferase-catalysed stereoselective glycosidation of monosaccharide-based glycosidase inhibitors: a new approach to the synthesis of sequence-specific glycosidase inhibitors
  作者：Christine Gautheron-Le Narvor、Chi-Huey Wong

  DOI：10.1039/c39910001130

  日期：——

  β-1,4-Galactosyltransferase was used as catalyst for galactosidation of 5-thioglucose, glucal and 1-deoxynojiriycin to form the corresponding β-1,4-galactosides as potential sequence-specific glycosidase inhibitors.

  以β-1,4-半乳糖基转移酶为催化剂，对 5-硫代葡萄糖、葡萄糖醛酸和 1-脱氧野尻霉素进行半乳糖化反应，生成相应的 β-1,4-半乳糖苷，作为潜在的序列特异性糖苷酶抑制剂。
• Enzymatic Synthesis of 4-<i>O</i>-<i>β</i>-<scp>D</scp>-Galactopyranosyl-moranoline and 3-<i>O</i>-<i>β</i>-<scp>D</scp>-Galacto-pyranosyl-moranoline by Using<i>β</i>-Galactosidase from<i>Bacillus circulans</i>
  作者：Masahiko Kojima、Takashi Seto、Yohsuke Kyotani、Hirotsugu Ogawa、Satoru Kitazawa、Kazuya Mori、Shigeaki Maruo、Tadaaki Ohgi、Yohji Ezure

  DOI：10.1271/bbb.60.694

  日期：1996.1

  A transgalactosyIation reaction from lactose to moranoline (1-deoxynojirimycin) was accomplished by using β-gaIactosidase [EC 3.2.1.23] from Bacillus circulans. The enzyme formed 3-O-β-D-galactopyranosyl-moranoline and 4-O-β-D-galactopyranosyl-moranoline as major products, together with 2-O-β-D-galactopyranosyl-moranoline and 6-O-β-D-galactopyranosyl-moranoline as minor ones.

  利用环状芽孢杆菌中的β-半乳糖苷酶[EC 3.2.1.23]，完成了从乳糖到吗啉（1-脱氧野尻霉素）的半乳糖化反应。该酶的主要产物是 3-O-β-D 吡喃半乳糖基-毛兰碱和 4-O-β-D-吡喃半乳糖基-毛兰碱，次要产物是 2-O-β-D 吡喃半乳糖基-毛兰碱和 6-O-β-D-吡喃半乳糖基-毛兰碱。
• 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.
• Wong, Chi-Huey; Ichikawa, Yoshitaka; Krach, Thomas, Journal of the American Chemical Society, 1991, vol. 113, # 21, p. 8137 - 8145
  作者：Wong, Chi-Huey、Ichikawa, Yoshitaka、Krach, Thomas、Narvor, Christine Gautheron-Le、Dumas, David P.、Look, Gary C.

  DOI：——

  日期：——
• Concise synthesis of 1-deoxy-4- O -β- d -galactopyranosyl- d -nojirimycin avoiding a glycosylation step
  作者：Felicia D'Andrea、Giorgio Catelani、Manuela Mariani、Barbara Vecchi

  DOI：10.1016/s0040-4039(00)02165-1

  日期：2001.2

  2',6'-Di-O-benzyl-2,3:5,6:3',4'-tri-O-isopropylidenelactose dimethyl acetal was used as starting material for the preparation of the until now unknown 4-O-beta -D-galactopyranosyl-D-xylo-hexos-5-ulose derivatives 7-9, through selective C-5 oxidation of its partially deprotected derivatives 4-6. Hydrolysis of 7-9 with aq. CF3COOH led to deprotected 1,5-dicarbonyl disaccharides 11-12, diastereoselectively transformed without purification into 1-deoxy-4-O-beta -D-galactopyranosyl-D-nojirimycin derivatives in about 60% yield, through a double reductive amination reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.