二脱水甘露醇 | 19895-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 二脱水甘露醇
• 英文名称: 1,2:5,6-dianhydro-D-mannitol
• 英文别名: Dianhydromannitol；(1S,2S)-1,2-bis[(2R)-oxiran-2-yl]ethane-1,2-diol
• CAS: 19895-66-0
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: AAFJXZWCNVJTMK-KVTDHHQDSA-N

物化性质

• 沸点：
  185.74°C (rough estimate)
• 密度：
  1.0945 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  65.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2905499000

反应信息

• 作为反应物：
  描述：

  二脱水甘露醇 在 盐酸 、 lithium bromide 作用下， 生成 二溴甘露醇
  参考文献：
  名称：

  由取代的己糖醇形成环氧化物

  摘要：

  摘要将1,6-二溴-1,6-二脱氧半乳糖醇（2），1-O-甲磺酰基-D-甘露醇（5）和3,4-二-O-甲磺酰基-D-甘露醇（8）分别转化为接近中性的pH值进入1,2：5,6-二脱水半乳糖醇（4），1,2-脱水D-甘露糖醇（6）和2,3：4,5-二脱水D-ID糖醇（9）。强碱性条件由1，6-二-O-甲磺酰基-D-甘露糖醇（1）产生2,3：4,5-二脱水-L-ID醇（7）。化合物4、6、7和9的结构通过pmr光谱及其对硫代硫酸根和碘离子的反应性得到了证实。1,2：5,6-二脱水-D-甘露醇（3）转化为1,6-二脱氧-1,6-二碘-D-甘露醇，1,6-二溴-1,6-二脱氧-D-描述了甘露糖醇和1，6-二-O-苯甲酰基-D-甘露糖醇和1,2：5,6-二脱水半乳糖醇成1,6-二脱氧-1,6-二碘代半乳糖醇。

  DOI：

  10.1016/s0008-6215(00)82130-8
• 作为产物：
  描述：

  甘露醇 在 吡啶 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 生成 二脱水甘露醇
  参考文献：
  名称：

  氨基糖：立体化学，环大小和N-取代物对葡萄糖苷酶活性的影响。

  摘要：

  N-取代的亚氨基糖类似物是强力的葡糖苷酶和糖基转移酶抑制剂，具有广泛的治疗应用，例如糖尿病和高雪氏病的治疗，免疫抑制活性以及对HIV，HPV，丙型肝炎，牛腹泻（BVDV），埃博拉病毒（Ebola）的抗菌和抗病毒作用EBOV）和马尔堡病毒（MARV），流行性感冒，寨卡病毒和登革热病毒。基于我们先前在功能化异构体1,5-二氧-1,5-亚氨基-D-古洛糖醇（L-古洛哌啶，在C-2和C-5处相对于葡萄糖或脱氧野oji霉素（DNJ）呈反向构型）的研究）和N-连接到吡喃葡萄糖单元不同位点的1,6-二脱氧-1,6-亚氨基-D-甘露醇（D-甘露聚糖-庚烷衍生物）核心，我们继续对这些带有简单N-烷基链而不是葡萄糖的亚氨基糖进行研究，以了解这些容易获得的支架是否可以保留相应的基于葡萄糖的N-烷基衍生物作为miglustat和miglitol药物中的DNJ核心的抑制谱。因此，通过利用经由两个异构体双环氧化物的S

  DOI：

  10.3390/ph12030108

文献信息

• CuAAC click chemistry with N-propargyl 1,5-dideoxy-1,5-imino-D-gulitol and N-propargyl 1,6-dideoxy-1,6-imino-D-mannitol provides access to triazole-linked piperidine and azepane pseudo-disaccharide iminosugars displaying glycosidase inhibitory properties
  作者：Luís Otávio B. Zamoner、Valquíria Aragão-Leoneti、Susimaire P. Mantoani、Michael D. Rugen、Sergey A. Nepogodiev、Robert A. Field、Ivone Carvalho

  DOI：10.1016/j.carres.2016.04.020

  日期：2016.6

  separable mix of piperidine N-propargyl 1,5-dideoxy-1,5-imino-D-gulitol and azepane N-propargyl 1,6-dideoxy-1,6-imino-D-mannitol. In O-acetylated form, these two building blocks were subjected to CuAAC click chemistry with a panel of three differently azide-substituted glucose building blocks, producing iminosugar pseudo-disaccharides in good yield. The overall panel of eight compounds, plus 1-deoxynojirimycin

  1,2：5,6-二脱水-D-甘露糖醇的无保护基合成，然后用炔丙基胺开环，随后闭环产生哌啶N-炔丙基1,5-二甲氧基-1,5的可分离混合物-亚氨基-D-古洛糖醇和氮杂环庚烷N-炔丙基1,6-二脱氧-1,6-亚氨基-D-甘露糖醇。以O-乙酰化形式，将这两个结构单元与一组三个不同的叠氮化物取代的葡萄糖结构单元进行CuAAC点击化学反应，以高收率生产亚氨基糖假二糖。评估了八种化合物的总含量，再加上1-脱氧野rim霉素（DNJ）作为基准，被评估为杏仁β-葡萄糖苷酶，酵母α-葡萄糖苷酶和大麦β-淀粉酶的前瞻性抑制剂。亚氨基糖假二糖对杏仁β-葡萄糖苷酶没有抑制活性，而母体N-炔丙基1,5-二脱氧-1，同样证明5-亚氨基-D-古洛糖醇和N-炔丙基1,6-二脱氧-1,6-亚氨基-D-甘露糖醇对酵母α-葡糖苷酶无活性。在以前的系列中，可以通过在氮上进行适当的取代来恢复其抑制活性。哌啶的更大活性可以基于对接研究
• Mechanisms of Formation of Adducts from Reactions of Glycidaldehyde with 2‘-Deoxyguanosine and/or Guanosine
  作者：Bernard T. Golding、Pritpal K. Slaich、Gordon Kennedy、Christine Bleasdale、William P. Watson

  DOI：10.1021/tx950057c

  日期：1996.1.1

  formed from guanosine and glycidaldehyde. The structure analysis of this adduct was also aided by 13C NMR analysis of the 15N-labeled adduct derived from [1-15N]guanosine. Analogous adducts were obtained from the reaction between glycidaldehyde and deoxyguanosine. Mechanisms of formation of the adducts from glycidaldehyde and guanosine/deoxyguanosine are proposed and supported by model studies with simple

  描述了由rac-but-3-ene-1,2-二醇方便地合成rac-缩水甘油醛和由D-甘露糖醇方便地合成（R）-缩水甘油醛。（R）-乙二醛（1）在水中与鸟嘌呤反应（pH 4-11，在较高pH下反应更快），最初产生6（S）-羟基-7（S）-（羟甲基）-3-（β-D -呋喃核糖基）-5,6,7-三氢咪唑并[1,2-α嘌呤-9（3H）-一（7a）和6（S），7（R）-二羟基-3-（β-D-呋喃核糖基）-5,6,7,8-四氢嘧啶基[1,2-α]嘌呤-10（3H）-一（8a）。前者分解为7-（羟甲基）-5,9-二氢-9-氧代-3-（β-D-核呋喃糖基）咪唑并[1,2-α]嘌呤（1,2-α）嘌呤（3a），5,9-二氢-9-氧代-3-（β-D-呋喃呋喃糖基）咪唑并[1,2-α]嘌呤（5a，1，N2-乙鸟嘌呤）和甲醛，而后者的加合物相对稳定。羟甲基在7-（羟甲基）-5的咪唑环上的位置 通过13 C NMR分
• Solid phase synthesis of (R)- and monoxide
  作者：David J Claffey、James A Ruth

  DOI：10.1016/s0957-4166(97)00537-5

  日期：1997.11

  A stereospecific route to (R)- and (S)-[C-13]-butadiene monoxide was developed using (R)- or (S)-glycidaldehyde and a polymer-supported Wittig reagent. (C) 1997 Elsevier Science Ltd.
• C2-symmetric enantiopure bis-α,β-butenolides as diastereoselective substrates in ethylene photocycloaddition
  作者：Pedro de March、Marta Figueredo、Josep Font、Javier Raya

  DOI：10.1016/s0040-4039(99)00172-0

  日期：1999.3

  Several C-2-symmetric bis-alpha,beta-butenolides have been synthesised starting from D-mannitol. Their [2+2]-photocycloaddition to ethylene has been studied as a model reaction to evaluate the influence of the protecting groups of the central diol system on the facial diastereoselectivity. The trimethylsilyl derivative shows the highest selectivity. The bis-cyclobutane containing products have been converted into the enantiopure adducts of gamma-hydroxymethyl-alpha,beta-butenolide and ethylene. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Hyperbranched polymers derived from anhydrosugar-related compounds and process for the preparation thereof
  申请人：Kaga Harumi

  公开号：US20050010023A1

  公开（公告）日：2005-01-13

  The hyperbranched polymers are at least one anhydrosugar-related compound selected from the dianhydrosugar alcohol [1]: (wherein R is hydrogen atom or a hydrocarbon group having from 1 to 30 carbon atoms, provided that nR's are equal to or different from one another and at least one R of nR's is hydrogen atom, and symbol n is an integer from 1 to 10) and the anhydrosugar alcohol [2]: (wherein each of R 1 , R 2 , R 3 and R 4 is hydrogen atom or a hydrocarbon group having from 1 to 30 carbon atoms; provided that R 1 , mR 2 's, pR 3 's and R 4 are equal to or different from one another and at least one R 2 or R 3 of said mR 2 's and pR 3 's is hydrogen atom, respectively; and symbol m is zero (0) or an integer from 1 to 20 and symbol p is an integer from 1 to 20, provided that symbol m+p is an integer from 1 to 20) or at least one anhydrosugar-related compound selected from the dianhydrosugar alcohol [1] and/or the anhydrosugar alcohol [2] with at least one sugar compound selected from the anhydrosugar as represented by the general formula [3], [4], [5], [6] or [7]. The hyperbranched polymers are readily prepared by polymerizing the dianhydrosugar alcohol or the anhydrosugar [1] or [2] or the dianhydrosugar alcohol or the anhydrosugar [1] or [2] together with the anhydrosugar in the presence of a cationic or anionic initiator.