1,6-anhydro-3,4-dideoxy-β-D-erythro-hex-3-enopyranose | 58394-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 1,6-anhydro-3,4-dideoxy-β-D-erythro-hex-3-enopyranose
• 英文别名: 1,6-anhydro-3,4-dideoxy-beta-D-erythro-hex-3-enopyranose；(1S,4R,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-ol
• CAS: 58394-28-8
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: LPADRPJZOJHCDL-KVQBGUIXSA-N

物化性质

• 沸点：
  262.7±40.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3,4-dideoxy-β-D-erythro-hex-3-enopyranose 在 manganese(IV) oxide 作用下， 以80%的产率得到左旋葡萄糖酮
  参考文献：
  名称：

  Shibagaki, Makoto; Takahashi, Kyoko; Kuno, Hideyuki, Chemistry Letters, 1990, # 2, p. 306 - 310

  摘要：

  DOI：
• 作为产物：
  描述：

  左旋葡萄糖酮 在 甲醇 、 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 21.0h， 生成 1,6-anhydro-3,4-dideoxy-β-D-erythro-hex-3-enopyranose
  参考文献：
  名称：

  操纵左葡萄糖苷的烯酮部分：1,3-移位反应，包括导致异左葡萄糖苷的反应

  摘要：

  描述了与生物质衍生的，高手性的和现在丰富的化合物左葡糖醛酮（1）相关的烯酮部分的操作。尽管衍生自烯丙醇3和4的三氯乙酰亚氨酸酯无法参与Overman型重排，但某些酯衍生物在Pd [0]催化剂存在下反应生成β，γ-不饱和丙二酸酯或酮的区域异构混合物，通过单晶X射线分析证实了其结构。在涉及1，3-转位反应的其他序列中，描述了用于将化合物1转化为异硫葡糖苷（2）的操作上简单的方法。 下载：下载高分辨率图片（51KB） 下载：下载全图

  DOI：

  10.1016/j.tet.2018.03.023

文献信息

• Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone
  作者：Xinghua Ma、Xin Liu、Patrick Yates、Warwick Raverty、Martin G. Banwell、Chenxi Ma、Anthony C. Willis、Paul D. Carr

  DOI：10.1016/j.tet.2018.03.023

  日期：2018.9

  The manipulation of the enone moiety associated with the biomass-derived, homochiral and now abundant compound levoglucosenone (1) is described. While the trichloroacetimidates derived from the allylic alcohols 3 and 4 failed to engage in Overman-type rearrangements, certain ester derivatives reacted in the presence of Pd[0]-catalysts to give regio-isomeric mixtures of β,γ-unsaturated malonates or

  描述了与生物质衍生的，高手性的和现在丰富的化合物左葡糖醛酮（1）相关的烯酮部分的操作。尽管衍生自烯丙醇3和4的三氯乙酰亚氨酸酯无法参与Overman型重排，但某些酯衍生物在Pd [0]催化剂存在下反应生成β，γ-不饱和丙二酸酯或酮的区域异构混合物，通过单晶X射线分析证实了其结构。在涉及1，3-转位反应的其他序列中，描述了用于将化合物1转化为异硫葡糖苷（2）的操作上简单的方法。 下载：下载高分辨率图片（51KB） 下载：下载全图
• Synthesis of 2-amino derivatives of levoglucosenone
  作者：F. A. Valeev、L. Kh. Kalimullina、Sh. M. Salikhov、O. V. Shitikova、I. P. Tsypysheva、M. G. Safarov

  DOI：10.1007/s10600-005-0052-8

  日期：2004.11

  2-Amino derivatives of levoglucosenone were prepared by reaction of the 2-methanesulfonyl (or p-toluenesulfonyl) derivatives with ammonia, methylamine, or octylamine under various conditions. The analogous reaction did not occur for saturated derivative 15. The 2-amino-3,4-dihydro derivative was prepared by catalytic hydrogenation of unsaturated amine 9.

  2-氨基衍生物的levoglucosenone是通过2-甲基磺酰基（或对甲苯磺酰基）衍生物与氨、甲胺或辛胺在不同条件下反应制备的。类似的反应在饱和衍生物15中没有发生。2-氨基-3,4-二氢衍生物是通过不饱和胺9的催化氢化制备的。
• Immuno-suppressive agent
  申请人：Ishihara Sangyo Kaisha Ltd.

  公开号：US05380834A1

  公开（公告）日：1995-01-10

  An immuno-suppressive agent containing, as an effective component, an, enopyranose derivative of the following formula (I) or its salt: ##STR1## wherein R.sup.1 is a hydrogen atom, alkyl which may be substituted, alkenyl, alkynyl, --OSO.sub.2 R.sup.7, a halogen atom, --OCOR.sup.7, --NHCOR.sup.8, alkoxy, phenyl which may be substituted or a saccharose residue, R.sup.2 is a hydrogen atom or alkyl, R.sup.3 is a hydrogen atom or a halogen atom, R.sup.4 is a hydrogen atom, --COR.sup.9, silyl which may be substituted or alkyl which may be substituted, one of R.sup.5 and R.sup.6 is hydroxyl, alkoxy which may be substituted, a saccharose residue, cycloalkyloxy which may be substituted or --OCOR.sup.10 and the other is a hydrogen atom or alkyl which may be substituted, or R.sup.4 and R.sup.5 together form a single bond, while R.sup.6 is a hydrogen atom or alkyl which may be substituted, each of R.sup.7, R.sup.9 and R.sup.10 is alkyl or phenyl which may be substituted, R.sup.8 is alkyl, phenyl which may be substituted or benzyloxy, X is a hydrogen atom, alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, cycloalkyl which may be substituted, phenyl which may be substituted, pyridyl which may be substituted, furanyl which may be substituted, thienyl which may be substituted, formyl, --COR.sup.11, --C(W.sup.1)W.sup.2 R.sup.11 or --SO.sub.2 R.sup.11, R.sup.11 is a chain hydrocarbon group which may be substituted, a monocyclic hydrocarbon group which may be substituted, a polycyclic hydrocarbon group which may be substituted, a monocyclic heterocycle group which may be substituted, or a polycyclic heterocycle group which may be substituted, W.sup.1 is an oxygen atom or a sulfur atom, W.sup.2 is an oxygen atom, a sulfur atom or --NH--, Y is a hydrogen atom, alkyl which may be substituted, alkenyl which may be substituted or alkynyl which may be substituted.

  一种免疫抑制剂，其有效成分为以下式（I）或其盐的烯酮吡喃糖衍生物： ##STR1## 其中，R.sup.1是氢原子，可被取代的烷基，烯基，炔基，--OSO.sub.2R.sup.7，卤原子，--OCOR.sup.7，--NHCOR.sup.8，烷氧基，可被取代的苯基或蔗糖残基，R.sup.2是氢原子或烷基，R.sup.3是氢原子或卤原子，R.sup.4是氢原子，--COR.sup.9，可被取代的硅基或可被取代的烷基，R.sup.5和R.sup.6中的一个是羟基，可被取代的烷氧基，蔗糖残基，可被取代的环烷氧基或--OCOR.sup.10，另一个是氢原子或可被取代的烷基，或者R.sup.4和R.sup.5结合形成单键，而R.sup.6是氢原子或可被取代的烷基，R.sup.7，R.sup.9和R.sup.10中的每一个是可被取代的烷基或苯基，R.sup.8是烷基，可被取代的苯基或苄氧基，X是氢原子，可被取代的烷基，可被取代的烯基，可被取代的炔基，可被取代的环烷基，可被取代的苯基，可被取代的吡啶基，可被取代的呋喃基，可被取代的噻吩基，甲酰基，--COR.sup.11，--C（W.sup.1）W.sup.2R.sup.11或--SO.sub.2R.sup.11，R.sup.11是可被取代的链烃基，可被取代的单环烃基，可被取代的多环烃基，可被取代的单环杂环基或可被取代的多环杂环基，W.sup.1是氧原子或硫原子，W.sup.2是氧原子，硫原子或--NH--，Y是氢原子，可被取代的烷基，可被取代的烯基或可被取代的炔基。
• Immuno-suppressing enepyranose derivatives
  申请人：ISHIHARA SANGYO KAISHA, LTD.

  公开号：EP0560055A1

  公开（公告）日：1993-09-15

  An immuno-suppressive agent containing, as an effective component, an enopyranose derivative of the following formula (I) or its salt: wherein R1 is a hydrogen atom, alkyl which may be substituted, alkenyl, alkynyl, -OSO2R7, a halogen atom, -OCOR7, -NHCOR8, alkoxy, phenyl which may be substituted or a saccharose residue, R2 is a hydrogen atom or alkyl, R3 is a hydrogen atom or a halogen atom, R4 is a hydrogen atom, -COR9, silyl which may be substituted or alkyl which may be substituted, one of R5 and R6 is hydroxyl, alkoxy which may be substituted, a saccharose residue, cycloalkyloxy which may be substituted or -OCOR10 and the other is a hydrogen atom or alkyl which may be substituted, or R4 and R5 together form a single bond, while R6 is a hydrogen atom or alkyl which may be substituted, each of R7, R9 and R10 is alkyl or phenyl which may be substituted, R8 is alkyl, phenyl which may be substituted or benzyloxy, X is a hydrogen atom, alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, cycloalkyl which may be substituted, phenyl which may be substituted, pyridyl which may be substituted, furanyl which may be substituted, thienyl which may be substituted, formyl, -COR11, -C(W1)W2R11 or -SO2R11, R11 is a chain hydrocarbon group which may be substituted, a monocyclic hydrocarbon group which may be substituted, a polycyclic hydrocarbon group which may be substituted, a monocyclic heterocycle group which may be substituted, or a polycyclic heterocycle group which may be substituted, W1 is an oxygen atom or a sulfur atom, W2 is an oxygen atom, a sulfur atom or -NH-, Y is a hydrogen atom, alkyl which may be substituted, alkenyl which may be substituted or alkynyl which may be substituted.

  一种含有下式(I)的烯吡喃糖衍生物或其盐作为有效成分的免疫抑制剂： 其中 R1 是氢原子、可被取代的烷基、烯基、炔基、-OSO2R7、卤素原子、-OCOR7、-NHCOR8、烷氧基、可被取代的苯基或糖残基；R2 是氢原子或烷基；R3 是氢原子或卤素原子；R4 是氢原子、-COR9、可被取代的硅烷基或可被取代的烷基；R5 和 R6 中的一个是羟基、可被取代的烷氧基、糖残基、可被取代的环烷氧基或-OCOR10，另一个是氢原子或可被取代的烷基，或 R4 和 R5 一起形成单键，而 R6 是氢原子或可被取代的烷基，R7、R9 和 R10 各为烷基或可被取代的苯基，R8 是烷基、可被取代的苯基或苄氧基，X 是氢原子、可被取代的烷基，可被取代的烯基，可被取代的炔基，可被取代的环烷基，可被取代的苯基，可被取代的吡啶基，可被取代的呋喃基，可被取代的噻吩基，甲酰基，-COR11，-C(W1)W2R11 或-SO2R11，R11 是可被取代的链烃基，可被取代的单环烃基、W1 是氧原子或硫原子，W2 是氧原子、硫原子或-NH-，Y 是氢原子、可被取代的烷基、可被取代的烯基或可被取代的炔基。
• Catalytic production of 1,2,5,6-hexanetetrol from levoglucosenone
  申请人：Wisconsin Alumni Research Foundation

  公开号：US11247956B2

  公开（公告）日：2022-02-15

  A method of making of 1,2,5,6-hexanetetrol (“tetrol”). The method includes the steps of contacting a reaction solution containing water as well as levoglucosenone, dihydrolevoglucosenone, and/or levoglucosanol, with a catalyst containing metal and acid functionalities, at temperature of from about 100° C. to about 175° C., and a hydrogen partial pressure of from about 1 bar to about 50 bar (about 0.1 MPa to about 5 MPa), and for a time wherein at least a portion of the reactant is converted into 1,2,5,6-hexanetetrol.

  一种制造 1,2,5,6-己烷四醇（"四醇"）的方法。该方法包括以下步骤：将含有水以及左旋葡糖酮、二氢左旋葡糖酮和/或左旋葡糖醇的反应溶液与含有金属和酸官能团的催化剂接触，温度约为 100 摄氏度至约 175 摄氏度，氢分压约为 1 巴至约 50 巴（约 0.1 兆帕至约 5 兆帕），反应时间为一段时间，其中至少有一部分反应物转化为 1,2,5,6-己烷四醇。