1,2-bis<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>ethane | 127305-27-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-bis<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>ethane
• 英文别名: 3,4-dideoxy-1,2:5,6-di-O-isopropylidene-D-threo-hexitol；3,4-dideoxy-1,2;5,6-di-O-isopropylidene-D-threo-hexitol；(4S)-4-[2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 127305-27-5
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: JJFZEZAOYLHEQB-UWVGGRQHSA-N

物化性质

• 沸点：
  276.8±25.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>ethane 在 盐酸 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 (4S)-1,2-bis(2-phenyl-1,3-dioxolan-4-yl)ethane
  参考文献：
  名称：

  General entry to the 3,5-disubstituted indolizidine class of dendrobatid alkaloids. Total syntheses of both enantiomers of indolizidines 195B, 223AB, 239AB, and 239CD from a common chiral synthon

  摘要：

  DOI：

  10.1021/jo00045a034
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3,4-O-thioxocarbonyl-D-mannitol 在 Rh/Al₂O₃ 氢气 、 亚磷酸三乙酯 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 1,2-bis<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>ethane
  参考文献：
  名称：

  Asymmetric synthesis of trans-(2R,5R)-bis(benzyloxymethyl)pyrrolidine

  摘要：

  DOI：

  10.1016/s0040-4039(01)93858-4

文献信息

• Double Asymmetric Dihydroxylation of 1,5-Hexadiene
  作者：Martin E. Maier、Sebastian Reuter

  DOI：10.1002/jlac.199719971006

  日期：1997.10

  Double asymmetric dihydroxylation of 1,5-hexadiene gave in one step a mixture of the d,l/meso tetrols 6 in a ratio of 3.4:1. From this ratio a facial selectivity of 6.65:1 for each double bond can be calculated. As a consequence of the double reaction the d/l ratio can be estimated to be 44:1. Compound 6 served then as starting material for the preparation of the bis-epoxide 12 and the 2,5-dihydroxyhexane

  1，5-己二烯的双不对称二羟基化一步得到d，l /内消旋四元醇6的比例为3.4：1的混合物。根据该比率，可以计算出每个双键的面部选择性为6.65：1。由于双重反应的结果，d / l比可以估计为44：1。然后将化合物6用作制备双环氧化物12和2,5-二羟基己烷（13）的原料。尽管到目前为止还不可能分离非对映异构体，但是这种制备6、12和13的途径 可能仍然有用，因为它很短，并且衍生自它们的产品可能会导致关键分离。
• Asymmetric hydrogenation of &bgr;-keto esters
  申请人：BASF Aktienegesellschaft

  公开号：US06359165B1

  公开（公告）日：2002-03-19

  Enantiomerically pure &bgr;-hydroxy esters are prepared by a process in which &bgr;-keto esters are reacted with hydrogen in the presence of catalysts of the formula LRuX2 where X is halogen, acetate, allyl, methallyl, 2-phenylallyl, perchlorate, trifluoroacetate, tetrafluoroborate, hexafluoroantimonate, hexafluorophosphate, hexafluoroarsenate or trichloroacetate, L is a bidentate phospholane of the formula I  where B=a bridging link with 1-5 carbon atoms between the two phosphorus atoms, R1=H, C1-C6-alkyl, aryl, alkylaryl or SiR23, R2=alkyl or aryl, m=0 or 1, R3=H or OR4, and R4=R1, with the proviso that if m=1 then R3=H and if m=0 then R3 ≠ H.

  对映纯度的β-羟基酯通过以下过程制备：在催化剂LRuX2存在下，β-酮酯与氢反应，其中 X为卤素、乙酸酯、烯丙基、甲基烯丙基、2-苯基烯丙基、高氯酸盐、三氟乙酸盐、四氟硼酸盐、六氟锑酸盐、六氟磷酸盐、六氟砷酸盐或三氯乙酸盐， L为具有以下式I的双齿膦烷 其中 B=连接两个磷原子的1-5个碳原子的桥链， R1=H、C1-C6-烷基、芳基、烷基芳基或SiR23， R2=烷基或芳基， m=0或1， R3=H或OR4，以及 R4=R1， 但条件是如果m=1，则R3=H，如果m=0，则R3≠H。
• Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio-d-ribopyranosides as well as their 2-deoxy and 2,3-dideoxy derivatives possessing antithrombotic activity
  作者：Éva Bozó、Sándor Boros、János Kuszmann

  DOI：10.1016/s0008-6215(99)00175-5

  日期：1999.9

  1,2,3,4-Tetra-O-acetyl-5-thio-D-ribopyranose as well as its 1-bromide were used as donors in the reaction with 4-cyano- and 4-nitrobenzenethiol to give the corresponding thiogrycosides in different anomeric ratios depending on the reaction conditions. Zemplen deacetylation afforded 4-cyanophenyl as well as 4-nitrophenyl 1,5-dithio-alpha- and beta-D-ribopyranosides, respectively. 1,3,4-Tri-O-acetyl-2-deoxy-5-thio-D-erythro-pentopyranose was synthesized from methyl 2-deoxy-D-erythro-pentofuranoside and was coupled with 4-cyano- and 4-nitrobenzenethiol to give anomeric mixtures from which 4-cyanophenyl as well. as 4-nitrophenyl. 1,5-dithio-beta-D-erythro-pentopyranosides were isolated after deacetylation. 1,4-Di-O-acetyl-2,3-dideoxy-5-thio-D-glycero-pentopyranose was obtained starting from 1,2;5,6-di-O-isopropylidene-D-mannitol and used as the donor in the glycosylation reaction with 4-cyano- and 4-nitrobenzenethiol. The resulting anomeric mixtures were separated to give, after deacetylation, 4-cyanophenyl as well as 4-nitrophenyl 2,3-dideoxy-1,5-dithio-beta-D-glycero-pentopyranosides. All of these thioglycosides showed significant antithrombotic activity on rats after oral administration. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Verfahren zur asymmetrische Hydrierung von Beta-Ketoestern
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0992481B1

  公开（公告）日：2003-05-21
• HERSTELLUNG OPTISCH AKTIVER PHOSPHOLANE
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP1082328B1

  公开（公告）日：2002-11-20