6-amino-6-deoxy-D-glucitol | 134354-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-amino-6-deoxy-D-glucitol
• 英文别名: 6-amino-6-deoxy-D-sorbitol；1-amino-1-deoxy-D-sorbitol；D-glucamine；(2S,3R,4R,5R)-6-aminohexane-1,2,3,4,5-pentol
• CAS: 134354-65-7
• 化学式: C₆H₁₅NO₅
• 分子量: 181.189
• InChiKey: SDOFMBGMRVAJNF-JGWLITMVSA-N

物化性质

• 熔点：
  179-180 °C
• 沸点：
  530.7±50.0 °C(Predicted)
• 密度：
  1.506±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-amino-6-deoxy-D-glucitol 、 difluoroacetaldehyde N-tosylhydrazone 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以75%的产率得到
  参考文献：
  名称：

  [4 + 1] 原位生成的偶氮烯烃与胺的环化：获得 1-取代的 1,2,3-三唑的有效方法

  摘要：

  1-取代的 1,2,3-三唑代表许多临床药物的“特权”结构支架。然而，它们的传统制备方法主要依赖于具有潜在危险的乙炔和叠氮化物的热 [3 + 2] 环加成反应。在这里，我们报告了原位产生的偶氮烯烃的碱介导 [4 + 1] 环化从容易获得的二氟乙醛 N-甲苯磺酰腙 (DFHZ-Ts) 与胺在相对温和的条件下。这种不含叠氮化物和乙炔的策略提供了以区域特异性方式以高产率轻松获得各种 1-取代的 1,2,3-三唑衍生物的方法。这种转化具有很好的官能团耐受性，可以适应广泛的底物范围。此外，这种新方法在抗生素药物PH-027的克级合成和几种生物活性小分子和临床药物的后期衍生化中的应用证明了其普遍性、实用性和适用性。

  DOI：

  10.1016/j.cclet.2021.09.008
• 作为产物：
  描述：

  6-azido-6-deoxy-D-glucitol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到6-amino-6-deoxy-D-glucitol
  参考文献：
  名称：

  The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6

  摘要：

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.018

文献信息

• PRODUCTION OF CAPROLACTAM FROM CARBOHYDRATE-CONTAINING MATERIALS
  申请人：MURPHY Vincent J.

  公开号：US20120264908A1

  公开（公告）日：2012-10-18

  The present invention generally relates to processes for the conversion of glucose to caprolactam employing chemocatalytic oxidation and reduction reactions. The present invention also includes processes for the conversion of glucose to caprolactam via amido polyhydroxy acid products and amidocaproic acid or derivatives thereof. The present invention also includes processes that catalytically oxidize an amidopolyol to amidopolyhydroxy acid or derivatives thereof, and processes that catalytically hydrodeoxygenate amino or amido polyhydroxy acid or derivatives thereof to an amino or amidocaproic acid product. The amino or amidocaproic acid product may then be converted to caprolactam. The present invention also includes products produced by such processes and products producable from such products.

  本发明通常涉及将葡萄糖转化为己内酰胺的过程，利用化学催化氧化和还原反应。本发明还包括通过氨基多羟酸产品和氨基己酸或其衍生物将葡萄糖转化为己内酰胺的过程。本发明还包括催化氧化氨基多醇为氨基多羟酸或其衍生物的过程，以及催化氢解氨基或氨基多羟酸或其衍生物为氨基或氨基己酸产品的过程。然后，氨基或氨基己酸产品可以转化为己内酰胺。本发明还包括通过这些过程生产的产品和可从这些产品生产的产品。
• Synthesis of New N-Containing Maltooligosaccharides, .ALPHA.-Amylase Inhibitors, and Their Biological Activities.
  作者：Riichiro UCHIDA、Ayako NASU、Shoichi TOKUTAKE、Kouichi KASAI、Koichiro TOBE、Nobuyuki YAMAJI

  DOI：10.1248/cpb.47.187

  日期：——

  Fifteen new N-containing maltooligosaccharides were obtained using the chemoenzymatic method. Among these compounds, maltooligosaccharides having 6-amino-6-deoxy-D-sorbitol residue, (3R, 4R, 5R, 6S)-hexahydro-3, 4, 5, 6-tetrahydroxy-1H-azepine residue, and (3R, 5R)-3, 4, 5-trihydroxypiperidine residue at the reducing end showed strong inhibitory activities for human pancreatic α-amylase (HPA) (EC 3.2.1.1) and human salivary α-amylase (HSA). The administration of (3R, 4R, 5R, 6S)-hexahydro-3, 5, 6-trihydroxy-1H-azepine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (13, IC50=4.3×10-5M for HPA, IC50=8.2×10-5M for HSA) and (3R, 5R)-3, 5-dihydroxypiperidine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (18, IC50=3.4×10-5M for HPA, IC50=4.6×10-5M for HSA) to ICR mice suppressed postprandial hyperglycemia.

  利用化学酶法获得了 15 种新的含 N 的麦芽寡糖。在这些化合物中，还原端具有 6-氨基-6-脱氧-D-山梨醇残基、(3R, 4R, 5R, 6S)-hexahydro-3, 4, 5, 6-tetrahydroxy-1H-azepine 残基和 (3R, 5R)-3, 4, 5-trihydroxypiperidine 残基的麦芽寡糖对人胰腺α-淀粉酶（HPA）（EC 3.2.1.1）和人唾液α-淀粉酶（HSA）有很强的抑制活性。服用(3R, 4R, 5R, 6S)-六氢-3, 5, 6-三羟基-1H-氮杂卓-4-基 O-α-D-吡喃葡萄糖苷-(1→4)-α-D-吡喃葡萄糖苷（13，对 HPA 的 IC50=4.3×10-5M, 对 HSA 的 IC50=8.2×10-5M for HSA）和 (3R，5R)-3，5-二羟基哌啶-4-基 O-α-D-吡喃葡萄糖基-(1→4)-α-D-吡喃葡萄糖苷（18，IC50=3.4×10-5M for HPA，IC50=4.6×10-5M for HSA）给 ICR 小鼠服用可抑制餐后高血糖。
• A quantitative structure-reactivity relationship in N-acetyl oxazolidines: an electrostatic interaction controls rotamer population
  作者：R. Fernando Martínez、Martín Ávalos、Reyes Babiano、Pedro Cintas、José L. Jiménez、Juan C. Palacios、Esther M. S. Pérez

  DOI：10.1039/c0ob01039a

  日期：——

  The conformational population of Z and E isomers of the amide bond in N-acetyl oxazolidines is dictated by the electronic nature of the vicinal aryl ring. Experimental and theoretical data support a rationale based on a strong and stereodirecting charge–charge interaction that should be added to the arsenal of non-covalent interactions and whose influence can be more important than once thought.

  N-乙酰基恶唑烷中酰胺键的 Z 和 E 异构体的构象群由邻芳环的电子性质决定。实验和理论数据支持基于强立体定向电荷-电荷相互作用的基本原理，这种相互作用应该被添加到非共价相互作用的库中，并且其影响可能比以前想象的更重要。
• Water soluble sapphyrins: potential fluorescent phosphate anion sensors
  作者：Jonathan L. Sessler、Julian M. Davis、Vladimir Král、Thomas Kimbrough、Vincent Lynch

  DOI：10.1039/b306964h

  日期：——

  aggregated form and the concurrent formation of an anion-bound dimer with effective equilibrium constants on the order of 100-300 M(-1). In this study we show that at high phosphate-to-sapphyrin ratios in neutral, buffered aqueous solutions further deaggregation occurs to produce an anion-bound monomeric form. This highly fluorescent species is formed with effective equilibrium constants on the order of 6-19

  作为研究各种介质中皂苷的阴离子结合特性的一项持续性工作，在甲醇和缓冲的中性水溶液中研究了许多先前报道的水溶性皂苷，发现在这些溶液相条件下它们会发生自聚集。通过紫外线聚集和荧光光谱研究了自聚集产生的物种的性质及其形成过程。在以前的工作中（V.Král，H。Furuta，K。Shreder，V。Lynch和JL Sessler，J。Am。Chem。Soc。1996，118 1595-1607），发现添加了磷酸根型阴离子在pH值为6时溶于水溶性的山茱ap。图1引起可见光谱变化，该变化与结合到聚集形式以及同时形成具有100-300 M（-1）量级有效平衡常数的阴离子结合二聚体相一致。在这项研究中，我们表明，在中性，缓冲水溶液中，高磷酸盐/腰果粉比例时，会发生进一步的解聚，从而产生阴离子结合的单体形式。这种高度荧光的物质形成的有效平衡常数大约为6-19 M（-1），导致人们认为红枫素可以用作荧光磷酸
• US5541341A
  申请人：——

  公开号：US5541341A

  公开（公告）日：1996-07-30