Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester | 869107-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester
• 英文别名: Bn(-2)[Bn(-3)][Tf(-4)][Bn(-6)]Gal(b)-O-Ph(4-OMe)；[(2R,3S,4R,5R,6S)-6-(4-methoxyphenoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl] trifluoromethanesulfonate
• CAS: 869107-20-0
• 化学式: C₃₅H₃₅F₃O₉S
• 分子量: 688.719
• InChiKey: BHAHPLLKBRXILQ-BWNLSPMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester 在 水 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 123.0h， 生成 4-methoxyphenyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  经由Triflylation和后续处理与含水Stereocongested碳环醇的Stereoinversion Ñ，Ñ二甲基甲酰胺

  摘要：

  报道了一种适用于立体拥挤的碳环底物的仲醇立体转化的便利方法。一个简单的三步程序，包括羟基的三氟甲基化，通过用N，N-二甲基甲酰胺（DMF）水溶液处理引起的亲核氧取代和甲醇分解，可在一锅中有效立体异构化各种底物，包括糖衍生物。

  DOI：

  10.1021/acs.orglett.6b02675
• 作为产物：
  描述：

  4-甲氧苯基2,6-二-O-苄基-β-D-吡喃葡萄糖苷 在 吡啶 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.5h， 生成 Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  A Facile Method for β-Selenoglycoside Synthesis Using β-p-Methylbenzoyl Selenoglycoside as the Selenating Unit

  摘要：

  The reaction between alpha-glycosyl bromides and potassium p-methylselenobenzoate yields beta-p-methylbenzoyl selenoglycosides. The acyl selenoglycosides were activated by the action of a secondary amine and CS2CO3 to produce an anomeric selenolate anion, which reacted in situ with various electrophiles to yield novel selenoglycosides while retaining the anomeric stereochemistry.

  DOI：

  10.1021/ol051804s

文献信息

• On-water synthesis of glycosyl selenocyanate derivatives and their application in the metal free organocatalytic preparation of nonglycosidic selenium linked pseudodisaccharide derivatives
  作者：Tapasi Manna、Anup Kumar Misra

  DOI：10.1039/d1ra00711d

  日期：——

  Glycosyl selenocyanate derivatives were prepared in very good yield by the treatment of glycosyl halide or triflate derivatives with potassium selenocyanate in water. A variety of selenium linked pseudodisaccharide derivatives were prepared in excellent yield using glycosyl selenocyanates as stable building blocks in the presence of hydrazine hydrate under metal-free organocatalytic reaction conditions

  通过用硒氰酸钾在水中处理糖基卤化物或三氟甲磺酸酯衍生物，以非常好的产率制备了糖基硒氰酸酯衍生物。在水合肼存在下，在无金属有机催化反应条件下，使用糖基硒氰酸酯作为稳定的结构单元，以优异的产率制备了多种硒连接的假二糖衍生物。
• Stereoselective synthesis of various α-selenoglycosides using in situ production of α-selenolate anion
  作者：Masahiro Nanami、Hiromune Ando、Yumiko Kawai、Mamoru Koketsu、Hideharu Ishihara

  DOI：10.1016/j.tetlet.2006.12.056

  日期：2007.2

  alkyl and aryl selenoglycosides, selenoglycosyl amino acid and selenodisaccharide have been synthesized in a stereoselective manner. The key precursor of α-anomeric selenolate anion was designed as p-methylbenzoyl selenoglycoside, which was synthesized by the reaction of β-glycosyl chloride with potassium p-methylselenobenzoate. Upon the action of piperazine or methylhydrazine in the presence of Cs2CO3

  已经以立体选择的方式合成了多种α-硒代糖苷，包括烷基和芳基硒代糖苷，硒代糖基氨基酸和亚硒二糖。α异头selenolate阴离子的关键前体被设计为p -methylbenzoyl selenoglycoside，其通过β-糖基氯与钾反应，合成p -methylselenobenzoate。在Cs 2 CO 3的存在下，哌嗪或甲基肼的作用下，酰基硒代糖苷产生异头型硒酸根阴离子，其与各种亲电子部分原位反应生成α-硒代糖苷。
• Stereoinversion of Stereocongested Carbocyclic Alcohols via Triflylation and Subsequent Treatment with Aqueous <i>N</i>,<i>N</i>-Dimethylformamide
  作者：Hidenori Ochiai、Takashi Niwa、Takamitsu Hosoya

  DOI：10.1021/acs.orglett.6b02675

  日期：2016.12.2

  stereocongested carbocyclic substrates, is reported. A simple three-step procedure, including triflylation of the hydroxy group, nucleophilic oxygenative displacement by the treatment with aqueous N,N-dimethylformamide (DMF), and methanolysis, allowed for efficient stereoinversion of various substrates, including sugar derivatives, in one pot.

  报道了一种适用于立体拥挤的碳环底物的仲醇立体转化的便利方法。一个简单的三步程序，包括羟基的三氟甲基化，通过用N，N-二甲基甲酰胺（DMF）水溶液处理引起的亲核氧取代和甲醇分解，可在一锅中有效立体异构化各种底物，包括糖衍生物。
• A Facile Method for β-Selenoglycoside Synthesis Using β-<i>p</i>-Methylbenzoyl Selenoglycoside as the Selenating Unit
  作者：Yumiko Kawai、Hiromune Ando、Hideya Ozeki、Mamoru Koketsu、Hideharu Ishihara

  DOI：10.1021/ol051804s

  日期：2005.10.1

  The reaction between alpha-glycosyl bromides and potassium p-methylselenobenzoate yields beta-p-methylbenzoyl selenoglycosides. The acyl selenoglycosides were activated by the action of a secondary amine and CS2CO3 to produce an anomeric selenolate anion, which reacted in situ with various electrophiles to yield novel selenoglycosides while retaining the anomeric stereochemistry.