allo-inositol | 643-10-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allo-inositol
• 英文别名: D-allo-inositol；myo-inositol；allo-inositol；allo-Inosit；alloinositol
• CAS: 643-10-7
• 化学式: C₆H₁₂O₆
• 分子量: 180.158
• InChiKey: CDAISMWEOUEBRE-OQYPVSDDSA-N

物化性质

• 熔点：
  270-280 °C (dec.) (lit.)
• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -3.83
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  121.38
• 氢给体数：
  6.0
• 氢受体数：
  6.0

安全信息

• 海关编码：
  2906199090
• WGK Germany：
  3

制备方法与用途

合成方法：异肌醇二硼酸酯转化为异肌醇是通过盐酸介导的水解完成的。此工艺生成两当量的氯化钠和硼酸。反应在10体积的1N盐酸中于85-95℃进行，随后结晶可获得高纯度产品，其收率为60-65%，纯度大于99.9%（HPLC）。

反应信息

• 作为反应物：
  描述：

  allo-inositol 生成 2,4,6/3,5-pentahydroxycyclohexanone
  参考文献：
  名称：

  Anderson et al., Archives of Biochemistry, 1958, vol. 78, p. 518,520

  摘要：

  DOI：
• 作为产物：
  描述：

  山梨醇 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 吡啶 、 sodium tetrahydroborate 、 草酰氯 、 氢气 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 、 mineral oil 为溶剂， 反应 78.42h， 生成 allo-inositol
  参考文献：
  名称：

  Synthesis of allo- and epi-Inositol via the NHC-Catalyzed Carbocyclization of Carbohydrate-Derived Dialdehydes

  摘要：

  A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.

  DOI：

  10.1021/jo500645z

文献信息

• Method for producing water-soluble saccharide conjugates and saccharide mimetics by diels-alder reaction
  申请人：——

  公开号：US20040059101A1

  公开（公告）日：2004-03-25

  The present invention relates to a method by which saccharide compounds can be prepared in a very easy way. This method comprises the steps of: (a) attaching at least one saccharide to a cyclic or acyclic diene, (b) reacting the saccharide-containing diene obtained in step (a) or a commercially available saccharide-containing diene with a dienophile by Diels-Alder reaction.

  本发明涉及一种可以非常容易地制备糖类化合物的方法。该方法包括以下步骤： (a) 将至少一种糖类连接到环状或非环状二烯， (b) 通过Diels-Alder反应，将步骤（a）中获得的含糖二烯或商业上可获得的含糖二烯与二烯受体反应。
• Deoxygenation of Biomass-Derived Feedstocks: Oxorhenium-Catalyzed Deoxydehydration of Sugars and Sugar Alcohols
  作者：Mika Shiramizu、F. Dean Toste

  DOI：10.1002/anie.201203877

  日期：2012.8.6

  important for the conversion of biomass into chemicals and fuels. The methyltrioxorhenium‐catalyzed deoxydehydration reaction was successfully applied to this purpose using another alcohol as solvent/reductant. The reaction was highly stereospecific, affording linear polyene products from C4–C6 sugar alcohols and aromatic compounds from C4–C6 sugars.

  将糖转变为油：糖部分的脱氧反应对于将生物质转化为化学物质和燃料非常重要。使用另一种醇作为溶剂/还原剂，成功地将甲基三氧合or催化的脱氧脱水反应应用于此目的。该反应是高度立体，得到线性多烯的产品选自C 4 -C 6糖醇和芳族化合物选自C 4 -C 6克的糖。
• [EN] NITROREDUCTASE-RELEASABLE PRO-DRUGS AND METHODS FOR USING THE SAME<br/>[FR] PRO-MÉDICAMENT À LIBÉRATION PAR NITRORÉDUCTASE ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：UNIV ARIZONA

  公开号：WO2020210175A1

  公开（公告）日：2020-10-15

  The present invention provides a nitroreductase-releasable pro-drug of Formula (I); where Ar1, m, n, Z, Y, L, and A are as defined herein, and methods for using and producing the same. Compound of formula (I) is useful in oral administration of the active pharmaceutical ingredient to the distal gut region of a subject to treat a wide variety of clinical conditions associated with distal gut region of a subject, such as colorectal cancer, inflammatory bowel disease (IBD), infectious diarrhea, bacterial infections, and bacterial overgrowth.

  本发明提供了一种硝基还原酶可释放的前药，其具有式(I)的结构；其中Ar1、m、n、Z、Y、L和A如本文所定义，以及使用和生产该前药的方法。式(I)化合物可用于口服给药活性药物成分至受试者的远端肠道区域，以治疗与远端肠道区域相关的多种临床状况，例如结直肠癌、炎症性肠病（IBD）、感染性腹泻、细菌感染和细菌过度生长。
• Simple and Efficient Routes to Optically Active<i>chiro</i>- and<i>allo</i>-Inositol Derivatives from<i>myo</i>-Inositol
  作者：Yutaka Watanabe、Kana M. Sureshan

  DOI：10.1055/s-2004-815443

  日期：——

  Efficient routes for the gram scale syntheses of optically active chiro- and allo-inositol derivatives from readily available 1,2:4,5-di-O-isopropylidene-myo-inositol (1) are described. Both d and l forms of these isomeric inositols could be synthesized from enantiomers of 1. One-pot methodology for the simultaneous synthesis of both chiro and allo has also been developed. The possible selectivity for the cleavage of trans-ketal in presence of the cis is an added advantage for the syntheses of a variety of protected deri­vatives for phosphoinositol syntheses. These routes provide synthetically flexible 1,2:4,5-di-O-isopropylidene-chiro-inositol and 1,6:3,4-di-O-isopropylidene-allo-inositol which are difficult to achieve otherwise.

  描述了从易得的1,2:4,5-二-O-异丙基烯醇-myoinositol（1）合成光学活性的手性和异手性肌醇衍生物的高效路线。这些异构肌醇的d和l形式可以通过1的对映体合成。还开发了一种一锅法，可以同时合成手性和异手性化合物。在存在顺式的情况下，反式酮的断裂选择性是合成多种保护衍生物用于磷脂酰肌醇合成的一个额外优势。这些路线提供了合成灵活的1,2:4,5-二-O-异丙基烯醇手性肌醇和1,6:3,4-二-O-异丙基烯醇异手性肌醇，这些在其他方法中难以实现。
• General synthesis of inositols by hydrolysis of conduritol epoxides obtained biocatalytically from halogenobenzenes: (+)-D-chiro-inositol, allo-inositol, muco-inositol and neo-inositol
  作者：Martin Mandel、Tomas Hudlicky

  DOI：10.1039/p19930000741

  日期：——

  Four of the nine isomeric inositols have been prepared by hydrolytic opening of epoxides derived from 3-halogenocyclohexa-3,5-diene-1,2-diol by further oxidation with potassium permanganate or by reduction of chiro-3-inosose (2L-2,3,6/4,5-pentahydroxycyclohexanone).

  九个异构体肌醇的四个已制备通过用高锰酸钾通过进一步氧化由3- halogenocyclohexa -3,5-二烯-1,2-二醇衍生的环氧化物的水解或开口通过还原的手性-3-肌糖（2大号- 2,3,6 / 4,5-五羟基环己酮）。

表征谱图