folic acid dimethyl ester benzenesulfonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: folic acid dimethyl ester benzenesulfonate
• 英文别名: (S)-folic acid dimethylester benzenesulfonic acid；αS-folic acid dimethyl ester benzenesulfonate；benzenesulfonic acid;dimethyl (2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioate
• 化学式: C₆H₆O₃S*C₂₁H₂₃N₇O₆
• 分子量: 627.635
• InChiKey: XJZUQCZVEXLEJO-UQKRIMTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  250
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  folic acid dimethyl ester benzenesulfonate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate daniphos chiral ligand 、 氢气 作用下， 以 甲醇 为溶剂， 70.0 ℃ 、8.0 MPa 条件下， 反应 17.0h， 以81.5%的产率得到tetrahydrofolic acid dimethylester
  参考文献：
  名称：

  Diastereoselective hydrogenation of folic acid esters with the Daniphos ligand

  摘要：

  Folic acid dimethylester benzenesulfonate was hydrogenated homogeneously in a rhodium-catalyzed diastereoselective reaction employing a set of the previously published planar-chiral "Daniphos" ligands, which are based on an arene chromium tricarbonyl scaffold. Diastereoselectivities of Lip to 42% de were achieved, almost matching the benchmark ligand BINAP. An X-ray structure of the most successful ligand P(i-Pr-2)/PPh2 is presented and discussed. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.11.026
• 作为产物：
  描述：

  folate 、 苯磺酸 以 甲醇 为溶剂， 反应 0.5h， 以86%的产率得到folic acid dimethyl ester benzenesulfonate
  参考文献：
  名称：

  Process for the preparation of pure stereoisomers of tetrahydrofolic acid esters salts and tetrahydrofolic acid by fractionated crystallization of tetrahydrofolic acid esters salts

  摘要：

  一种制备和浓缩(6S,αS)或(6S,αR)四氢叶酸酯盐和(6S,αS)或(6S,αR)四氢叶酸的过程，其特征在于，在有机溶剂中制备或溶解四氢叶酸酯的异构体加成盐与芳香磺酸的等摩尔或浓缩混合物，然后至少结晶一次，然后如适用，水解结晶物以产生(6S,αS)或(6S,αR)四氢叶酸，将后者结晶为自由酸或以盐的形式分离。

  公开号：

  US06858731B1

文献信息

• Process For The Preparation Of Optically Pure Tetrahydropterins And Derivatives, And Specifically Of Optically Pure Tetrahydrofolic Acid And Derivatives Thereof, By Stereospecific Hydrogenation
  申请人：MULLER Hans Rudolf

  公开号：US20080306263A1

  公开（公告）日：2008-12-11

  Process for the preparation of tetrahydropterin and tetrahydropterin derivatives by hydrogenating pterin and pterin derivatives with hydrogen in the presence of a hydrogenating catalyst, in which the hydrogenation is carried out in a polar reaction medium and metal complexes that are soluble in the reaction medium are employed as the hydrogenation catalysts. The process is suited to the hydrogenation, particularly asymmetric hydrogenation, of folic acid, folio acid salts, folio acid esters, folio acid ester salts or dihydroforms thereof, with the proviso that in the event of using folic acid, carboxylic acid salts thereof or dihydroforms thereof the reaction medium is aqueous, and in the event of using folic acid esters, folic acid ester salts or dihydroforms thereof the reaction medium is an alcohol. The process opens up straightforward access to achiral and chiral pterin derivatives.

  通过在存在氢化催化剂的情况下，用氢气氢化葉酸和葉酸衍生物制备四氢生物葉酸和四氢生物葉酸衍生物的过程，其中氢化是在极性反应介质中进行的，并且可溶于反应介质的金属配合物被用作氢化催化剂。该过程适用于葉酸、葉酸盐、葉酸酯、葉酸酯盐或其二氢形式的氢化，特别是不对称氢化，但若使用葉酸、其羧酸盐或二氢形式，则反应介质为水，若使用葉酸酯、葉酸酯盐或其二氢形式，则反应介质为醇。该过程为得到无手性和手性葉酸衍生物提供了直接途径。
• Stereoselective Hydrogenation of Folic Acid Dimethyl Ester Benzenesulfonate: A New Access to Optically PureL-Tetrahydrofolic Acid
  作者：Viola Groehn、Rudolf Moser、Benoît Pugin

  DOI：10.1002/adsc.200505098

  日期：2005.11

  Folic acid was converted to the corresponding dimethyl ester benzenesulfonate and stereoselectively hydrogenated in organic solvents. An extended screening with rhodium- and iridium-diphosphine catalysts was performed. Under optimized conditions the asymmetric hydrogenation provided a solution of tetrahydrofolic acid dimethyl ester with up to 44% de. The de could be increased to 98% by fractional crystallization

  将叶酸转化为相应的二甲基酯苯磺酸酯，并在有机溶剂中进行立体选择性氢化。用铑和铱二膦催化剂进行了扩展筛选。在优化的条件下，不对称氢化提供了高达44％de的四氢叶酸二甲酯溶液。通过从氢化混合物中分步结晶L-四氢叶酸二甲基酯苯磺酸盐，de可以提高到98％。酯的水解得到光学纯的L-四氢叶酸，可以将其分离或转化为其5-或10-或5,10-取代的衍生物。
• VERFAHREN ZUR HERSTELLUNG VON OPTISCH REINEN TETRAHYDROPTERINEN UND DERIVATEN, IM SPEZIELLEN OPTISCH REINER TETRAHYDROFOLSÄURE UND IHREN DERIVATEN, DURCH STEREOSPEZIFISCHE HYDRIERUNG
  申请人：EPROVA AG Forschungsinstitut

  公开号：EP1200437B1

  公开（公告）日：2004-03-10
• Diastereoselective hydrogenation of folic acid esters with the Daniphos ligand
  作者：Wolfgang Braun、Beatrice Calmuschi-Cula、Albrecht Salzer、Viola Groehn

  DOI：10.1016/j.jorganchem.2005.11.026

  日期：2006.5

  Folic acid dimethylester benzenesulfonate was hydrogenated homogeneously in a rhodium-catalyzed diastereoselective reaction employing a set of the previously published planar-chiral "Daniphos" ligands, which are based on an arene chromium tricarbonyl scaffold. Diastereoselectivities of Lip to 42% de were achieved, almost matching the benchmark ligand BINAP. An X-ray structure of the most successful ligand P(i-Pr-2)/PPh2 is presented and discussed. (c) 2005 Elsevier B.V. All rights reserved.
• Process for the preparation of pure stereoisomers of tetrahydrofolic acid esters salts and tetrahydrofolic acid by fractionated crystallization of tetrahydrofolic acid esters salts
  申请人：Muller Hans Rudolf

  公开号：US06858731B1

  公开（公告）日：2005-02-22

  A process for preparing and concentrating (6S,αS) or (6S,αR) tetrahydrofolic acid ester salts and (6S,αS) or (6S,αR) tetrahydrofolic acid, characterized by preparing or dissolving equimolar or concentrated mixtures of diastereomers of addition salts of tetrahydrofolic acid esters with aromatic sulphonic acids in organic solvents, followed by crystallizing them at least once, and then if applicable hydrolyzing the crystallizate to produce (6S,αS) or (6S,αR) tetrahydrofolic acid, crystallizing the latter as a free acid or isolating it in the form of a salt.

  一种制备和浓缩(6S,αS)或(6S,αR)四氢叶酸酯盐和(6S,αS)或(6S,αR)四氢叶酸的过程，其特征在于，在有机溶剂中制备或溶解四氢叶酸酯的异构体加成盐与芳香磺酸的等摩尔或浓缩混合物，然后至少结晶一次，然后如适用，水解结晶物以产生(6S,αS)或(6S,αR)四氢叶酸，将后者结晶为自由酸或以盐的形式分离。