2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]-dioxol-(6S)-ol | 18439-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]-dioxol-(6S)-ol
• 英文别名: 1,2-O-isopropylidene-5-phenyl-5-deoxy-α-D-xylofuranose；(3aR,5R,6S,6aR)-5-benzyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 18439-39-9
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: XJHVBSUUMAEOGV-YVECIDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]-dioxol-(6S)-ol 在 偶氮二异丁腈 、 硫酸 、 三正丁基氢锡 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 6.5h， 生成 5-phenylmethyl-(2SR,3R,5R)-tetrahydrofuran-2,3-diol
  参考文献：
  名称：

  Synthesis of harzialactone A and its isomers from d-glucose and assignment of absolute stereochemistry

  摘要：

  The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned unambiguously. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00389-x
• 作为产物：
  描述：

  phenylmagnesium bromide 、 1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose 以 四氢呋喃 为溶剂， 以83%的产率得到2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]-dioxol-(6S)-ol
  参考文献：
  名称：

  Synthesis of harzialactone A and its isomers from d-glucose and assignment of absolute stereochemistry

  摘要：

  The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned unambiguously. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00389-x

文献信息

• NOVEL DERIVATIVES OF ACYL CYANOPYRROLIDINES
  申请人：Akolkar Nakul Pramod

  公开号：US20120040897A1

  公开（公告）日：2012-02-16

  A compound of formula (I) or a tautomeric form, regioisomer, stereoisomer, solvate, N-oxide or pharmaceutically acceptable salts thereof; wherein ‘a’—is selected from the group consisting of substituted or unsubstituted heterocycloalkyl ring and substituted or unsubstituted carbohydrate moiety y is a member selected from —O—, —CO—, —S02-, aminoalkyl or formula (II) wherein, R w is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl; x is a member selected from -0-, —S—, —SO—, —S02-, CONR10, NR10CO and —NR d —, or x and y together represent a chemical bond; Z is selected from —CH—, —N—. t is an integer selected from O to 4; with the provisos that when ‘a’ is substituted or unsubstituted heterocycloalkyl ring then ‘t’ is not O and when y=—CO—, x is not NR d .

  化合物的公式（I）或其互变异构体，区域异构体，立体异构体，溶剂化物，N-氧化物或其药学上可接受的盐；其中，‘a’选择自取代或未取代的杂环烷基环或取代或未取代的碳水化合物基团，y为成员选择自—O—，—CO—，—S02-，氨基烷基或公式（II）其中，Rw为氢，取代或未取代的烷基，烯基，炔基，环烷基，芳基，杂环芳基；x为成员选择自-0-，—S—，—SO—，—S02-，CONR10，NR10CO和—NRd—，或x和y一起表示化学键；Z选择自—CH—，—N—。 t为整数，选择自0到4；条件是当‘a’为取代或未取代的杂环烷基环时，‘t’不为0，当y=—CO—时，x不为NRd。
• 5-Deoxy-5-alkyl-1,2-O-isopropylidene-α-D-xylofuranoses as chiral auxiliaries in asymmetric 1,4-addition reaction
  作者：Yung-Son Hon、Fen-Ling Chen、Yih-Pyng Huang、Ta-Jung Lu

  DOI：10.1016/s0957-4166(00)82200-4

  日期：1991.1

  Two deoxy-sugar based chiral auxiliaries (2 and 5) have been prepared. Their alpha,beta-unsaturated esters were treated with different cuprate reagents to give the 1,4-addition adducts in good chemical yield and good diastereoselectivity.
• Synthesis of harzialactone A and its isomers from d-glucose and assignment of absolute stereochemistry
  作者：Hari Babu Mereyala、Maju Joe、Rajendrakumar Reddy Gadikota

  DOI：10.1016/s0957-4166(00)00389-x

  日期：2000.10

  The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned unambiguously. (C) 2000 Elsevier Science Ltd. All rights reserved.