((4R,5S)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolan-4-yl)methanol | 42927-35-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((4R,5S)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolan-4-yl)methanol
• 英文别名: ((2S,3R)-2,2-dimethyl-5-((4'R,5'S)-2',2',5'-trimethyl-1',3'-dioxolan-4'-yl)-1,3-dioxolan-4-yl)methanol；2,3:4,5-di-O-isopropylidene-L-fucitol；6-Deoxy-2,3:4,5-di-O-isopropyliden-L-galactitol；O²,O³;O⁴,O⁵-diisopropylidene-D-1-deoxy-galactitol；O²,O³;O⁴,O⁵-Diisopropyliden-D-1-desoxy-galactit；[(4R,5S)-2,2-dimethyl-5-[(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]-1,3-dioxolan-4-yl]methanol
• CAS: 42927-35-5
• 化学式: C₁₂H₂₂O₅
• 分子量: 246.304
• InChiKey: NYRAALXXZIFOQZ-JLIMGVALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((4R,5S)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolan-4-yl)methanol 在 氢氧化钾 、 potassium permanganate 作用下， 生成 O²,O³;O⁴,O⁵-diisopropylidene-L-fuconic acid ; potassium-salt
  参考文献：
  名称：

  Akiya; Suzuki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 1296

  摘要：

  DOI：
• 作为产物：
  描述：

  山梨酸乙酯 在 四氧化锇 、 (DHQ)2-PHAL 、 甲基磺酰胺 、 potassium carbonate 四氧化锇 、 甲基磺酰胺 、 camphor-10-sulfonic acid 、 二异丁基氢化铝 、 potassium carbonate 、 对甲苯磺酸 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 39.5h， 生成 ((4R,5S)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolan-4-yl)methanol
  参考文献：
  名称：

  Enantioselective Synthesis of 10-epi-Anamarine via an Iterative Dihydroxylation Sequence

  摘要：

  The enantioselective syntheses of 10-epi-anamarine and 5,10-epi,epi-anamarine have been achieved in 13 to 14 steps. The route relies upon an enantio- and regioselective Sharpless dihydroxylation of either dienoates or trienoates to establish the C-8 to C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route also relies upon a ring-closing metathesis to establish the alpha,beta-unsaturated lactones.

  DOI：

  10.1021/ol047322i

文献信息

• METHOD FOR PRODUCING L-FUCOSE
  申请人：Schroven Andreas

  公开号：US20130245250A1

  公开（公告）日：2013-09-19

  Method for producing L-fucose includes in a first aspect, a method for the preparation of L-fucose, wherein L-fucose precursors are produced from pectin and L-fucose is produced from the L-fucose precursors; in a second aspect, a method for the preparation of L-fucose from D-galacturonic acid or a salt thereof, wherein L-fucose precursors are produced from D-galacturonic acid of a salt thereof, and L-fucose is produced from the L-fucose precursors; and an L-fucose precursor as shown in Formula A, wherein R is a linear or branched chain saturated hydrocarbon group with 1-6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, etc., preferably a methyl group.

  生产L-岩藻糖的方法包括第一方面，一种制备L-岩藻糖的方法，其中L-岩藻糖前体从果胶中产生，并且L-岩藻糖从L-岩藻糖前体中产生；第二方面，一种从D-半乳糖酸或其盐制备L-岩藻糖的方法，其中L-岩藻糖前体从D-半乳糖酸或其盐中产生，并且L-岩藻糖从L-岩藻糖前体中产生；以及如公式A所示的L-岩藻糖前体，其中R是线性或支链饱和碳原子数为1-6的烷基羟基烃基，例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、正丁基、叔丁基、正己基等，最好是甲基。
• [EN] METHOD FOR PRODUCING L-FUCOSE<br/>[FR] PROCÉDÉ DE PRODUCTION DE L-FUCOSE
  申请人：GLYCOM AS

  公开号：WO2012049257A1

  公开（公告）日：2012-04-19

  The present invention provides: in a first aspect, a method for the preparation of L-fucose, wherein L-fucose precursors are produced from pectin and L-fucose is produced from the L-fucose precursors; in a second aspect, a method for the preparation of L-fucose from D-galacturonic acid or a salt thereof, wherein L-fucose precursors are produced from D-galacturonic acid or a salt thereof, and L-fucose is produced from the L-fucose precursors; and an L-fucose precursoras shown in Formula A below, wherein R is a linear or branched chain saturated hydrocarbon group with 1-6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, etc., preferably a methyl group.

  本发明提供：在第一方面，一种制备L-岩藻糖的方法，其中L-岩藻糖前体从果胶中产生，L-岩藻糖从L-岩藻糖前体中产生；在第二方面，一种从D-半乳糖醛酸或其盐制备L-岩藻糖的方法，其中L-岩藻糖前体从D-半乳糖醛酸或其盐中产生，L-岩藻糖从L-岩藻糖前体中产生；以及如下所示的L-岩藻糖前体，其中R是具有1-6个碳原子的线性或支链饱和碳氢化合物基团，如甲基、乙基、正丙基、异丙基、正丁基、异丁基、正丁基、叔丁基、正己基等，优选为甲基。
• De Novo Asymmetric Synthesis of Anamarine and Its Analogues
  作者：Dong Gao、George A. O'Doherty

  DOI：10.1021/jo051681p

  日期：2005.11.1

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.
• The Structure of Diacetone-L-fucitol (2,3,4,5-Di-isopropylidene-L-fucitol)
  作者：A. T. Ness、Raymond M. Hann、C. S. Hudson

  DOI：10.1021/ja01256a067

  日期：1942.4
• Enantioselective Synthesis of 10-<i>e</i><i>pi</i>-Anamarine via an Iterative Dihydroxylation Sequence
  作者：Dong Gao、George A. O'Doherty

  DOI：10.1021/ol047322i

  日期：2005.3.1

  The enantioselective syntheses of 10-epi-anamarine and 5,10-epi,epi-anamarine have been achieved in 13 to 14 steps. The route relies upon an enantio- and regioselective Sharpless dihydroxylation of either dienoates or trienoates to establish the C-8 to C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route also relies upon a ring-closing metathesis to establish the alpha,beta-unsaturated lactones.