6-Desoxy-L-allit | 18545-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Desoxy-L-allit
• 英文别名: 1-deoxy-D-allitol；D-1-deoxy-allitol；1-deoxy L-allitol；1-deoxy D-allitol；(2R,3R,4S,5S)-hexane-1,2,3,4,5-pentol
• CAS: 18545-98-7
• 化学式: C₆H₁₄O₅
• 分子量: 166.174
• InChiKey: SKCKOFZKJLZSFA-BGPJRJDNSA-N

物化性质

• 沸点：
  468.0±40.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-Desoxy-L-allit 在 Enterobacter aerogenes IK₇ 作用下， 以 水 为溶剂， 生成 1-deoxy-D-psicose
  参考文献：
  名称：

  Conversion of l-rhamnose into ten of the sixteen 1- and 6-deoxyketohexoses in water with three reagents: d-tagatose-3-epimerase equilibrates C3 epimers of deoxyketoses

  摘要：

  The efficient isomerization of L-rhamnose [the only cheaply available deoxy hexose] to 1-deoxy-L-psicose, 1-deoxy-D-psicose, 1-deoxy-L-fructose, 1-deoxy-D-fructose, 1-deoxy-L-tagatose, 6-deoxy-L-psicose, 6-deoxy-D-psicose, 6-deoxy-L-fructose, 6-deoxy-D-fructose, and 6-deoxy-L-tagatose is described. The conversion of rhamnose to ten of the sixteen 1- and 6-deoxyketohexoses is accomplished in water in three steps. The range of substrates for D-tagatose-3-epimerase (DTE) is extended to 1- and 6-deoxyketoses. An authentic sample of 6-deoxy-D-psicose is prepared from D-psicose. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.024
• 作为产物：
  描述：

  (+/-)-(3SR,4RS,5SR,6RS)-3-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-6-methyl-1,2-dioxane-4,5-diol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以75%的产率得到6-Desoxy-L-allit
  参考文献：
  名称：

  Osmium Catalyzed Dihydroxylation of 1,2-Dioxines:  A New Entry for Stereoselective Sugar Synthesis

  摘要：

  A series of 3,6-substituted 3,6-dihydro-1,2-dioxines were dihydroxylated with osmium tetroxide to furnish 1,2-dioxane-4,5-diols (peroxy diols) in yields ranging from 33% to 98% and with de values not less than 90%. The peroxy diols were then reduced to generate a stereospecific tetraol core with R, R, S, S or "allitol" stereochemistry. The peroxy diols and their acetonide derivatives were also ring-opened with Co(II) salen complexes to give novel hydroxy ketones in 77-100% yield, including the natural sugar psicose. Importantly, preliminary work on the catalytic asymmetric ring-opening of meso-peroxy diols using the Co(II) Jacobsens's catalyst indicates that asymmetric sugar synthesis from 1,2-dioxines is possible.

  DOI：

  10.1021/jo060949p

文献信息

• DEOXYKETOHEXOSE ISOMERASE AND METHOD FOR PRODUCING DEOXYHEXOSE AND DERIVATIVE THEREOF USING SAME
  申请人：Izumori Ken

  公开号：US20100105885A1

  公开（公告）日：2010-04-29

  Providing 1- or 6-deoxy products corresponding to all of aldohexoses, ketohexoses and sugar alcohols, as based on Deoxy-Izumoring, as well as a method for systematically producing those products. A method for producing deoxyketohexose and a derivative thereof using a deoxyketohexose isomerase derived from Pseudomonas cichorii ST-24 (FERM BP-2736), comprising epimerizing 1-deoxy D-ketohexose or 6-deoxy D-ketohexose or 1-deoxy L-ketohexose or 6-deoxy L-ketohexose at position 3 to produce the individually corresponding 1-deoxy D-ketohexose or 6-deoxy D-ketohexose or 1-deoxy L-ketohexose or 6-deoxy L-ketohexose as an intended product.

  提供对应于所有己醛糖、己酮糖和糖醇的1-或6-去氧产物，基于去氧-Izumoring，以及一种系统生产这些产物的方法。一种使用来自Pseudomonas cichoriiST-24（FERM BP-2736）的去氧己酮糖异构酶生产去氧己酮糖及其衍生物的方法，包括将1-去氧D-己酮糖或6-去氧D-己酮糖或1-去氧L-己酮糖或6-去氧L-己酮糖在3号位置上对映异构化为各自对应的1-去氧D-己酮糖或6-去氧D-己酮糖或1-去氧L-己酮糖或6-去氧L-己酮糖作为预期产物。
• Effect of carbon chain length on catalytic C O bond cleavage of polyols over Rh-ReOx/ZrO2 in aqueous phase
  作者：Achraf Sadier、Noémie Perret、Denilson Da Silva Perez、Michèle Besson、Catherine Pinel

  DOI：10.1016/j.apcata.2019.117213

  日期：2019.9

  -tetraols, -triols, -diols, and hexanols) is achievable by hydrogenolysis of erythritol, xylitol, and sorbitol over supported-bimetallic Rh-ReOx (Re/Rh molar ratio 0.5) catalyst, respectively. After validation of the analytical methodology, the effect of some reaction parameters was studied. In addition to CO bond cleavage by hydrogenolysis, these polyols can undergo parallel reactions such as epimerization

  线性脱氧的C4（丁三醇，-二醇和丁醇），C5（戊四醇，-三醇，-二醇和戊醇）和C6产品（己烷五醇，-四醇，-三醇，-二醇和己醇）的生产可以实现赤藓糖醇，木糖醇和山梨糖醇分别在负载型双金属Rh-ReO x（Re / Rh摩尔比0.5）催化剂上进行氢解。在验证了分析方法之后，研究了一些反应参数的影响。除了通过氢解裂解C O键外，这些多元醇还可以进行平行反应，例如差向异构化，循环脱水和CC键裂解。线性脱氧C4，C5和C6产品每个家族的时间进程证实，不同类别的脱氧产品的出现顺序遵循多重顺序的脱氧途径。在高压下，在3.7wt。％Rh-3.5wt。％ReO x / ZrO 2催化剂存在下，对线性脱氧的C4，C5和C6产物混合物的最高选择性在80％的转化率下是有利的（54–71％ 80 bar下）在200°C下。
• MICROORGANISM WITH ABILITY TO PRODUCE DEOXY POLYOL DEHYDROGENASE AND USE THEREOF
  申请人：Izumori Ken

  公开号：US20100167350A1

  公开（公告）日：2010-07-01

  Problem: To provide a microorganism with an ability to produce deoxy polyol dehydrogenase. Means for Resolution: A microorganism belonging to genus Enterobacter with an ability to produce a dehydrogenase for deoxy polyol of the same structure at the positions C2 and C3 as that of ribitol or L-iditol. The bacterial cell IK7 of the genus Enterobacter (accession No. NITE P-271). A method for producing deoxy ketose comprising allowing a culture containing the deoxy polyol dehydrogenase obtained by the culturing of the microorganism of the invention or allowing the deoxy polyol dehydrogenase to react with a solution containing deoxy polyol of the same structure at the positions C2 and C3 as that of ribitol or L-iditol to oxidize deoxy polyol to produce the corresponding deoxy ketose and then collecting the deoxy ketose. The deoxy polyol is 1-deoxy-D-allitol, while the corresponding deoxy ketose is 1-deoxy-L-psicose. Otherwise, the deoxy polyol is L-rhamnitol, while the corresponding deoxy ketose is 1-deoxy-L-fructose.

  问题：提供一种微生物具有产生脱氧多元醇脱氢酶的能力。 解决方法：一种属于肠杆菌属（Enterobacter）的微生物，具有在C2和C3位置与核糖醇或L-异鼠李糖具有相同结构的脱氢酶产生能力。该微生物为肠杆菌属的IK7细胞（存取号为NITE P-271）。一种生产脱氧酮糖的方法，包括使用含有本发明微生物培养产生的脱氧多元醇脱氢酶的培养物，或者让脱氧多元醇脱氢酶与含有与核糖醇或L-异鼠李糖在C2和C3位置具有相同结构的脱氧多元醇的溶液反应，将脱氧多元醇氧化为相应的脱氧酮糖，然后收集脱氧酮糖。其中，脱氧多元醇为1-脱氧-D-阿洛糖，相应的脱氧酮糖为1-脱氧-L-丝糖。否则，脱氧多元醇为L-鼠李糖，相应的脱氧酮糖为1-脱氧-L-果糖。
• Deoxyketohexose isomerase and method for producing deoxyhexose and derivative thereof using same
  申请人：Izumori Ken

  公开号：US08389248B2

  公开（公告）日：2013-03-05

  Providing 1- or 6-deoxy products corresponding to all of aldohexoses, ketohexoses and sugar alcohols, as based on Deoxy-Izumoring, as well as a method for systematically producing those products. A method for producing deoxyketohexose and a derivative thereof using a deoxyketohexose isomerase derived from Pseudomonas cichorii ST-24 (FERM BP-2736), comprising epimerizing 1-deoxy D-ketohexose or 6-deoxy D-ketohexose or 1-deoxy L-ketohexose or 6-deoxy L-ketohexose at position 3 to produce the individually corresponding 1-deoxy D-ketohexose or 6-deoxy D-ketohexose or 1-deoxy L-ketohexose or 6-deoxy L-ketohexose as an intended product.

  提供所有醛糖、酮糖和糖醇对应的1-或6-去氧产物，基于Deoxy-Izumoring，以及一种系统生产这些产物的方法。使用源自Pseudomonas cichorii ST-24 (FERM BP-2736)的去氧酮糖异构酶，包括在位置3上使1-去氧D-酮糖、6-去氧D-酮糖、1-去氧L-酮糖或6-去氧L-酮糖发生外消旋反应，以生产相应的1-去氧D-酮糖、6-去氧D-酮糖、1-去氧L-酮糖或6-去氧L-酮糖作为预期产物的方法。
• MICROORGANISM CAPABLE OF PRODUCING DEOXY POLYOL DEHYDROGENASE AND UTILIZATION OF THE SAME
  申请人：National University Corporation Kagawa University

  公开号：EP2096164A1

  公开（公告）日：2009-09-02

  Problem: To provide a microorganism with an ability to produce deoxy polyol dehydrogenase. Means for Resolution: A microorganism belonging to genus Enterobacter with an ability to produce a dehydrogenase for deoxy polyol of the same structure at the positions C2 and C3 as that of ribitol or L-iditol. The bacterial cell IK7 of the genus Enterobacter (accession No. NITE P-271). A method for producing deoxy ketose comprising allowing a culture containing the deoxy polyol dehydrogenase obtained by the culturing of the microorganism of the invention or allowing the deoxy polyol dehydrogenase to react with a solution containing deoxy polyol of the same structure at the positions C2 and C3 as that of ribitol or L-iditol to oxidize deoxy polyol to produce the corresponding deoxy ketose and then collecting the deoxy ketose. The deoxy polyol is 1-deoxy-D-allitol, while the corresponding deoxy ketose is 1-deoxy-L-psicose. Otherwise, the deoxy polyol is L-rhamnitol, while the corresponding deoxy ketose is 1-deoxy-L-fructose.

  问题：提供一种能够产生脱氧多元醇脱氢酶的微生物。 解决方法：一种属于肠杆菌属的微生物，能够产生一种脱氧多元醇脱氢酶，其 C2 和 C3 位的结构与核糖醇或 L-iditol的结构相同。肠杆菌属的细菌细胞 IK7（登录号：NITE P-271）。一种生产脱氧酮糖的方法，包括让含有通过培养本发明微生物而获得的脱氧多元醇脱氢酶的培养物或让脱氧多元醇脱氢酶与含有在C2和C3位上结构与核糖醇或L-iditol相同的脱氧多元醇的溶液反应，氧化脱氧多元醇以产生相应的脱氧酮糖，然后收集脱氧酮糖。脱氧多元醇是 1-脱氧-D-阿糖醇，而相应的脱氧酮糖是 1-脱氧-L-花生糖。否则，脱氧多元醇为 L-鼠李糖醇，而相应的脱氧酮糖为 1-脱氧-L-果糖。