6-Chloro-2,4,6-trideoxy-D-erythro-hexose | 163928-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Chloro-2,4,6-trideoxy-D-erythro-hexose
• 英文别名: chlorolactol；(3R,5S)-6-Chloro-3,5-dihydroxyhexanal
• CAS: 163928-25-4
• 化学式: C₆H₁₁ClO₃
• 分子量: 166.605
• InChiKey: ZRPLUEXPLPUZFP-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Chloro-2,4,6-trideoxy-D-erythro-hexose 在 溴 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 以82%的产率得到(4R,6S)-6-(chloromethyl)-4-hydroxytetrahydropyran-2-one
  参考文献：
  名称：

  Process for the preparation of 2-(6-subtituted-1,-3-dioxane-4-yl)acetic acid derivatives

  摘要：

  该发明涉及制备公式（1）中2-(6-取代-1,3-二氧杂环戊烷-4-基)乙酸衍生物，其中X代表一个脱离基团，R1、R2和R3各自独立地代表一个碳原子数为1-3的烷基基团，来自4-羟基-6-X-取代-甲基-四氢吡喃-2-酮化合物，其中X如上定义，借助缩醛化剂，在酸催化剂存在下进行。该发明还涉及公式（1）中的新化合物以及从中制备的盐和酸，其中公式（1）中的OR3基团被OY基团取代，其中X、R1和R2具有上述定义的含义，Y代表碱性（土）金属或取代或未取代的铵基团或代表氢，并涉及公式（2）的新化合物。所涉产品在转化为2-(6-羟甲基-1,3-二氧杂环戊烷-4-基)乙酸的叔丁基酯之后，在他汀类药物制备中作为中间体产品非常重要。

  公开号：

  US20030158426A1

文献信息

• [EN] A NOVEL, GREEN AND COST EFFECTIVE PROCESS FOR SYNTHESIS OF TERT-BUTYL (3R,5S)-6-OXO-3,5-DIHYDROXY-3,5-O-ISOPROPYLIDENE-HEXANOATE<br/>[FR] NOUVEAU PROCÉDÉ ÉCOLOGIQUE ET ÉCONOMIQUE POUR LA SYNTHÈSE DE TERT-BUTYL (3R,5S)-6-OXO-3,5-DIHYDROXY-3,5-O-ISOPROPYLIDÈNE-HEXANOATE
  申请人：LUPIN LTD

  公开号：WO2014203045A1

  公开（公告）日：2014-12-24

  The present invention provides a process of preparation of an intermediate useful for the preparation of statins more particularly the present invention relates to an eco-friendly and cost effective process for the preparation of tert -butyl (3R,5S)-6-oxo-3,5-dihydroxy- 3,5-O-isopropylidene-hexanoate [I].

  本发明提供了一种制备中间体的过程，该中间体用于制备他汀类药物，更具体地说，本发明涉及一种环保且具有成本效益的过程，用于制备叔丁基(3R,5S)-6-氧化-3,5-二羟基-3,5- O-异丙基亚戊酸酯[I]。
• PROCESS FOR THE PREPARATION OF 2-(6-SUBSTITUTED-1,-3-DIOXANE-4-YL) ACETIC ACID DERIVATIVES
  申请人：KOOISTRA Jacob Hermanus Mattheus Hero

  公开号：US20110251406A1

  公开（公告）日：2011-10-13

  The invention relates to the preparation of 2-(6-substituted-1,3-dioxane-4-yl)acetic acid derivatives of formula (1), where X stands for a leaving group, and R 1 , R 2 , and R 3 each independently stand for an alkyl group with 1-3 carbon atoms from 4-hydroxy-6-X-substituted-methyl-tetrahydropyran-2-one compounds, where X is as defined above, with the aid of an acetalization agent, in the presence of an acid catalyst. The invention also relates to the novel compounds of formula (1) as well as salts and acids to be prepared from these, with the OR 3 group in formula (1) being replaced by an OY group, where X, R 1 and R 2 have the meanings defined above and where Y stands for an alkaline (earth) metal or a substituted or unsubstituted ammonium group or stands for hydrogen, and to the novel compounds of formula (2). The products concerned are, after conversion into the t-butyl ester of 2-(6-hydroxymethyl-1,3-dioxane-4-yl)acetic acid, important as intermediary products in the preparation of statins.

  本发明涉及利用缩酮化试剂，在酸催化剂的存在下，从4-羟基-6-X-取代甲基四氢吡喃-2-酮化合物中制备出通式（1）中的2-(6-取代-1,3-二氧杂环-4-基)乙酸衍生物，其中X代表离去基，R1、R2和R3各自独立地代表1-3个碳原子的烷基基团，其中X如上所定义。本发明还涉及通式（1）的新化合物以及从中制备的盐和酸，其中在通式（1）中的OR3基团被OY基团所取代，其中X、R1和R2具有上述定义，Y代表碱金属或取代或未取代的铵基团，或代表氢，并涉及通式（2）的新化合物。所述产品在转化为2-(6-羟甲基-1,3-二氧杂环-4-基)乙酸t-丁基酯后，在他汀类药物制备中作为中间体产品具有重要作用。
• [EN] PROCESS FOR THE PREPARATION OF 2-(6-SUBSTITUTED-1,3-DIOXANE-4-YL)ACETIC ACID DERIVATIVES<br/>[FR] PROCEDE DE PREPARATION DE DERIVES D'ACIDE 2-(1,3-DIOXANE-4-YL SUBSTITUE EN 6)ACETIQUE
  申请人：DSM NV

  公开号：WO2002006266A1

  公开（公告）日：2002-01-24

  The invention relates to the preparation of 2-(6-substituted-1,3-dioxane-4-yl)acetic acid derivatives of formula (1), where X stands for a leaving group, and R1, R2, and R3 each independently stand for an alkyl group with 1-3 carbon atoms from 4-hydroxy-6-X-substituted-methyl-tetrahydropyran-2-one compounds, where X is as defined above, with the aid of an acetalization agent, in the presence of an acid catalyst. The invention also relates to the novel compounds of formula (1) as well as salts and acids to be prepared from these, with the OR3 group in formula (1) being replaced by an OY group, where X, R1 and R2 have the meanings defined above and where Y stands for an alkaline (earth) metal or a substituted or unsubstituted ammonium group or stands for hydrogen, and to the novel compounds of formula (2). The products concerned are, after conversion into the t-butyl ester of 2-(6-hydroxymethyl-1,3-dioxane-4-yl)acetic acid, important as intermediary products in the preparation of statins.

  本发明涉及从4-羟基-6-X-取代甲基四氢吡喃-2-酮化合物（其中X代表离去基，R1、R2和R3分别独立地代表具有1-3个碳原子的烷基基团）中，在醛缩剂的帮助下，在酸催化剂的存在下制备公式（1）的2-（6-取代-1,3-二氧杂环-4-基）乙酸衍生物，所述公式（1）中OR3基团被OY基团取代，其中X、R1和R2具有上述定义，Y代表碱金属或取代或未取代的铵基团或代表氢，以及公式（2）的新化合物，本发明还涉及从这些化合物制备的盐和酸。所述产物在转化为2-（6-羟甲基-1,3-二氧杂环-4-基）乙酸叔丁酯后，作为合成他汀类药物的中间体物质具有重要作用。
• [EN] USE OF 2-DEOXYRIBOSE-5-PHOSPHATE ALDOLASE TO PREPARE 2-DEOXYFUCOSE, ANALOGUES AND DERIVATIVES<br/>[FR] UTILISATION DE 2-DESOXYRIBOSE-5-PHOSPHATE ALDOLASE POUR LA PREPARATION DE 2-DESOXYFUCOSE, D'ANALOGUES ET DE DERIVES.
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：WO1996031615A1

  公开（公告）日：1996-10-10

  (EN) Processes using 2-deoxyribose-5-phosphate aldolase (DERA) are described for the preparation of 2-deoxyfucose and related compounds. In one embodiment, DERA is used to catalyse the condensation of acetaldehyde as donor and a 2(R)-hydroxy-3-(hydroxy or mercapto)-propionaldehyde derivative to form a 2-deoxysugar whose hydroxyls have the configuration of fucose. In another embodiment, DERA is used to catalyze the condensation of two moles of acetaldehyde as donor and one mole of a 2-substituted acetaldehyde acceptor to form a 2,4,6-trideoxyhexose via a 4-substituted-3-hydroxybutanal intermediate.(FR) Procédés utilisant la 2-désoxyribose-5-phosphatealdolase (DERA) pour la préparation de 2-désoxyfucose et de composés associés. Selon un mode de réalisation, la DERA est utilisée pour catalyser la condensation de l'acétaldéhyde comme donneur et d'un dérivé de 2(R)-hydroxy-3-(hydroxy ou mercapto)-propionaldéhyde pour former un sucre 2-désoxy dont les hydroxyles ont la configuration du fucose. Selon un autre mode de réalisation, la DERA est utilisée pour catalyser la condensation de deux moles d'acétaldéhyde comme donneur et d'une mole d'un accepteur acétaldéhyde substitué en position 2 de façon à former un 2,4,6-tridésoxyhexose via un intermédiaire 4-substitué-3-hydroxybutanal.

  (ZH) 描述了使用2-脱氧核糖-5-磷酸醛缩酶（DERA）制备2-脱氧岩藻糖和相关化合物的过程。在一种实施方式中，DERA用于催化乙醛作为供体和2（R）-羟基-3-（羟基或巯基）-丙醛衍生物的缩合，形成一个2-去氧糖，其羟基具有岩藻糖的构型。在另一种实施方式中，DERA用于催化两摩尔乙醛作为供体和一摩尔2-取代乙醛受体的缩合，通过4-取代-3-羟基丁醛中间体形成一个2,4,6-三去氧己糖。
• Process for the Preparation of 2-(6-Substituted-1,3-Dioxane-4-yl)Acetic Acid Derivatives
  申请人：Kooistra Jacob Hermanus Mattheus Hero

  公开号：US20100136339A1

  公开（公告）日：2010-06-03

  The invention relates to the preparation of 2-(6-substituted-1,3-dioxane-4-yl)acetic acid derivatives of formula 1, where X stands for a leaving group, and R 1 , R 2 , and R 3 each independently stand for an alkyl group with 1-3 carbon atoms from 4-hydroxy-6-X-substituted-methyl-tetrahydropyran-2-one compounds, where X is as defined above, with the aid of an acetalization agent, in the presence of an acid catalyst. The invention also relates to the novel compounds of formula 1 as well as salts and acids to be prepared from these, with the OR 3 group in formula 1 being replaced by an OY group, where X, R 1 and R 2 have the meanings defined above and where Y stands for an alkaline (earth) metal or a substituted or unsubstituted ammonium group or stands for hydrogen, and to the novel compounds of formula 2. The products concerned are, after conversion into the t-butyl ester of 2-(6-hydroxymethyl-1,3-dioxane-4-yl)acetic acid, important as intermediary products in the preparation of statins.

  本发明涉及从4-羟基-6-X-取代-甲基-四氢吡喃-2-酮化合物（其中X代表离去基，而R1、R2和R3各自独立地代表1-3个碳原子的烷基）中，借助缩醛剂，在酸催化剂的存在下制备公式1中的2-(6-取代-1,3-二氧杂环-4-基)乙酸衍生物。本发明还涉及公式1中的新化合物以及从这些化合物制备的盐和酸，其中在公式1中OR3基团被OY基团替换，其中X、R1和R2具有上述定义，而Y代表碱金属或取代或未取代的铵基团或代表氢。此外，本发明还涉及公式2的新化合物。这些产品在转化为2-(6-羟甲基-1,3-二氧杂环-4-基)乙酸叔丁酯后，作为他汀类药物的中间体具有重要意义。