phenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thioa-β-D-pyranoside | 111425-48-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thioa-β-D-pyranoside
• 英文别名: phenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-β-D-pyranoside；phenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-1-thio-hex-2-enopyranoside；phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-β-D-erythro-hex-2-enopyranoside；phenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-1-thiohex-2-enopyranoside；4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-2-enopyranoside；[(2R,3S,6S)-3-acetyloxy-6-phenylsulfanyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 111425-48-0；125848-19-3；137740-45-5；111425-49-1
• 化学式: C₁₆H₁₈O₅S
• 分子量: 322.382
• InChiKey: CPPQXIRWLOCYDE-XHSDSOJGSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  438.7±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 phenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thioa-β-D-pyranoside 在 双(乙腈)氯化钯(II) 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.47h， 生成 methyl 4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl) 2,3,6-tris-O-(phenylmethyl)-α-D-glucopyranoside 、
  参考文献：
  名称：

  钯（II）的推荐Ô -Glycosylation涉及1-硫代-2- enosides和3-硫基-1- enoses

  摘要：

  ø thioglycosyl供体，2,3-二脱氧己-1-硫代-2- enopyranosides，1,2-二脱氧己-3-硫基-1- nopyranoses和2-吡啶基的-glycosylation 2,3,4,6-四ø苄基-1-硫代β- d吡喃葡萄糖苷通过使用其从双制备钯（II）的活化剂来实现（乙腈）二氯化钯（II）（加入Pd（CH 3 CN）2氯2）和三氟甲磺酸银（AgOTf）。

  DOI：

  10.1016/0040-4039(94)88180-4
• 作为产物：
  描述：

  乙酰化葡萄烯糖 、 苯硫酚 生成 phenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thioa-β-D-pyranoside
  参考文献：
  名称：

  VALVERDE, SERAFIN;GARCIA-OCHOA, SILVESTRE, J. CARBOHYDR. CHEM., 8,(1989) N, C. 553-563

  摘要：

  DOI：

文献信息

• Environmentally Benign Synthesis of 2,3-Unsaturated Glycopyranosides in Task-Specific Ionic Liquid
  作者：Goutam Guchhait、Anup Kumar Misra

  DOI：10.1007/s10562-011-0646-7

  日期：2011.7

  A green reaction condition has been developed for the synthesis of 2,3-unsaturated glycopyranosides by the Ferrier rearrangement of glycals using alcohols and thiols in 1-butyl-3-methylimidazolium trifluoromethanesulfonate ([BMIM]·OTf) in excellent yield. [BMIM]·OTf has been applied as a task specific ionic liquid organo-catalyst. Operational simplicity, environmentally benign reaction condition, use

  已经开发了一种绿色反应条件，通过在 1-丁基-3-甲基咪唑鎓三氟甲磺酸盐 ([BMIM]·OTf) 中使用醇和硫醇对糖类进行费里尔重排，以优异的收率合成 2,3-不饱和吡喃糖苷。[BMIM]·OTf 已被用作任务特定的离子液体有机催化剂。该方法的显着特点是操作简单、环境友好的反应条件、使用任务特定的离子液体、反应时间短、收率高。
• Alkylation and acylation of phenylthio 2,3-dideoxyhex-2-enopyranosides at the anomeric centre by polarity inversion
  作者：Serafín Valverde、Silvestre García-Ochoa、Manuel Martín-Lomas

  DOI：10.1039/c39870000383

  日期：——

  Alkylation and acylation of phenylthio 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside derivatives at the anomeric centre by polarity inversion give C-1 alkylated or acylated phenylthio 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides.

  烷基化和苯硫基-2,3-二脱氧α-酰化d -赤由极性反转给予C-1烷基化或酰化的苯硫基-2,3-二脱氧α-在异头中心-己-2-烯吡喃糖苷衍生物d -赤-己-2-烯吡喃糖苷。
• 3,5-Dinitrobenzoic acid catalyzed synthesis of 2,3-unsaturated O- and S-glycosides and tetrahydropyranylation of alcohols and phenols
  作者：Naganjaneyulu Bodipati、Srinivasa Rao Palla、Venkateshwarlu Komera、Rama Krishna Peddinti

  DOI：10.1016/j.tetlet.2014.10.093

  日期：2014.12

  A simple procedure for the synthesis of 2,3-unsaturated glycosides in acetonitrile and tetrahydropyranylation of alcohols and phenols in dichloromethane in the presence of 3,5-dinitrobenzoic acid is described. A variety of alcohols and thiols are reacted with glycals to give the desired products in high yields with high α-selectivity.

  描述了一种简单的程序，用于在乙腈中合成2,3-不饱和糖苷以及在3,5-二硝基苯甲酸存在下在二氯甲烷中将醇和酚进行四氢吡喃基化。使多种醇和硫醇与缩醛反应，以高收率和高α选择性得到所需产物。
• Nitrosyl Tetrafluoroborate Catalyzed Preparation of 2,3-Unsaturated Glycosides and 2-Deoxyglycosides of Hindered Alcohols, Thiols, and Sulfonamides
  作者：Anup Misra、Abhishek Santra、Goutam Guchhait

  DOI：10.1055/s-0032-1318406

  日期：——

  Nitrosyl tetrafluoroborate (NOBF4) has been successfully applied as an efficient organocatalyst for the preparation of 2,3-unsaturated and 2-deoxyglycosides of hindered alcohols, aryl thiols, and aryl sulfonamides from glycal derivatives under the Ferrier rearrangement conditions. Product yields and stereo-outcomes were very good.

  四氟硼酸亚硝基酯 (NOBF4) 已成功用作有效的有机催化剂，用于在费里尔重排条件下由糖基衍生物制备受阻醇、芳基硫醇和芳基磺酰胺的 2,3-不饱和和 2-脱氧糖苷。产品产量和立体效果非常好。
• Ferrier Rearrangement Catalyzed by HClO₄-SiO₂: Synthesis of 2,3-Unsaturated Glycopyranosides
  作者：Anup Kumar Misra、Pallavi Tiwari、Geetanjali Agnihotri

  DOI：10.1055/s-2004-837297

  日期：——

  Alkyl 2,3-unsaturated glycopyranosides have been prepared by the Ferrier rearrangement of acetyl protected glycals catalyzed by HClO 4 -SiO 2 . Operational simplicity, use of economically convenient catalyst, mild reaction conditions, high yields, short reaction times are the key features of this protocol.

  已通过 HClO 4 -SiO 2 催化乙酰保护糖基的 Ferrier 重排制备烷基 2,3-不饱和吡喃糖苷。操作简单、使用经济上方便的催化剂、温和的反应条件、高收率、短反应时间是该协议的主要特点。