benzyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-1-thiohex-2-enopyranoside | 557104-56-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-1-thiohex-2-enopyranoside
• 英文别名: benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside；[(2R,3S,6R)-3-acetyloxy-6-benzylsulfanyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 557104-56-0
• 化学式: C₁₇H₂₀O₅S
• 分子量: 336.409
• InChiKey: CHYNPSMVEBRFEQ-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  benzyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-1-thiohex-2-enopyranoside 、 乙酸酐 在 ruthenium trichloride 、 sodium periodate 、 水 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 反应 1.5h， 以69%的产率得到benzyl 2,3,4,6-tetra-O-acetyl-1-sulfonyl-α-D-mannopyranoside
  参考文献：
  名称：

  Pd催化烯丙基重排非对映选择性合成硫苷

  摘要：

  立体选择性糖基化在碳水化合物化学中具有挑战性。在此，通过钯催化的烯丙基重排对糖醛进行立体选择性硫代糖基化，可在 α-异构体硫糖苷上产生各种取代基。通过硫代硫酸盐与衍生自葡萄糖、阿拉伯糖、半乳糖和鼠李糖的糖苷的组合，获得了两个综合系列的芳基和苄基硫糖苷。此外，薯蓣基 α-l-鼠李糖苷和异槲皮苷分别通过 α-亚砜-鼠李糖苷和 α-亚砜-葡萄糖苷的立体特异性 [2,3]-σ 重排实现了选择性。

  DOI：

  10.1021/acs.orglett.1c03302
• 作为产物：
  描述：

  4,6-di-O-acetyl-D-glucal 在 吡啶 、 4-二甲氨基吡啶 、 1,1'-双(二苯基膦)二茂铁 、 bis(benzonitrile)palladium(II) chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 benzyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-1-thiohex-2-enopyranoside
  参考文献：
  名称：

  Pd催化烯丙基重排非对映选择性合成硫苷

  摘要：

  立体选择性糖基化在碳水化合物化学中具有挑战性。在此，通过钯催化的烯丙基重排对糖醛进行立体选择性硫代糖基化，可在 α-异构体硫糖苷上产生各种取代基。通过硫代硫酸盐与衍生自葡萄糖、阿拉伯糖、半乳糖和鼠李糖的糖苷的组合，获得了两个综合系列的芳基和苄基硫糖苷。此外，薯蓣基 α-l-鼠李糖苷和异槲皮苷分别通过 α-亚砜-鼠李糖苷和 α-亚砜-葡萄糖苷的立体特异性 [2,3]-σ 重排实现了选择性。

  DOI：

  10.1021/acs.orglett.1c03302

文献信息

• 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。
• Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)–C(3) Unsaturated and α-<scp>d</scp>-Mannopyranosyl Sulfones
  作者：Sravanthi Chittela、Thurpu Raghavender Reddy、Palakodety Radha Krishna、Sudhir Kashyap

  DOI：10.1021/acs.joc.5b00975

  日期：2015.7.17

  An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and a-p-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access alpha-n-mannopyranosyl sulfones in good yields with high regioselectivity.
• ZnCl2/alumina impregnation catalyzed Ferrier rearrangement: an expedient synthesis of pseudoglycosides
  作者：Bala Kishan Gorityala、Rujee Lorpitthaya、Yaguang Bai、Xue-Wei Liu

  DOI：10.1016/j.tet.2009.04.099

  日期：2009.7

  An improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated-O-glycosides with high alpha-selectivity. (C) 2009 Elsevier Ltd. All rights reserved.
• (S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides
  作者：Bala Kishan Gorityala、Shuting Cai、Jimei Ma、Xue-Wei Liu

  DOI：10.1016/j.bmcl.2009.04.003

  日期：2009.6

  A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid. (S)-CSA acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could be coupled with glucal to give the desired pseudoglycosides in good to excellent yields with exclusive alpha-stereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.
• Scope of AuCl3 in the activation of per-O-acetylglycals
  作者：Rengarajan Balamurugan、Srinivasa Rao Koppolu

  DOI：10.1016/j.tet.2009.07.087

  日期：2009.9

  Gold(III)chloride in catalytic amounts activates 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal, and 3,4-di-O-acetyl-L-rhamnal efficiently. The activated species can be employed in the Ferrier reaction with different nucleophiles at ambient conditions. Attempts have been made to make beta-anomer of the Ferrier product from anomeric-O-propargylated Ferrier product. (C) 2009 Elsevier Ltd. All rights reserved.