phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-D-erythro-hex-2-enopyranoside

• 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-1-thio-D-erythro-hex-2-enopyranoside
• 英文别名: ((3S)-3-acetoxy-6-(phenylthio)-3,6-dihydro-2H-pyran-2-yl)methyl acetate；phenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-1-thio-hex-2-enopyranoside；[(2R,3S)-3-acetyloxy-6-phenylsulfanyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• 化学式: C₁₆H₁₈O₅S
• 分子量: 322.382
• InChiKey: CPPQXIRWLOCYDE-QMRHZFGWSA-N

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：

  phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-D-erythro-hex-2-enopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium periodate 、 水 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 1.0h， 生成 phenyl 2,3,4,6-tetra-O-acetyl-1-sulfonyl-α-D-mannopyranoside
  参考文献：
  名称：

  Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)–C(3) Unsaturated and α-d-Mannopyranosyl Sulfones

  摘要：

  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.

  DOI：

  10.1021/acs.joc.5b00975
• 作为产物：
  描述：

  二苯二硫醚 、 乙酰化葡萄烯糖 在 aluminum (III) chloride 、 hafnium tetrakis(trifluoromethanesulfonate) 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以40%的产率得到phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Synthesis of 3-S- and 3-Se-glycals by using R-S-S-R and R-Se-Se-R as the nucleophile precursors promoted by Hf(OTf)4 and the temperature-dependent formation of the above-mentioned 3-S- and 3-Se products

  摘要：

  By using Hf(OTf)(4) as the catalyst, under certain conditions, reaction of tri-O-acetyl-D-glucal and ((2R,3S)-3-acetoxy-2,3-dihydrofuran-2-yl)methyl acetate with alkyl(aryl) bisulfide/alkyl(aryl) biselenide as nucleophile precursor leads to temperature-dependent formation of C-1-S/Se and C-3-S/Se product. A temperature-dependent profile of the yield of these two products is given. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.151648

文献信息

• An Efficient Method for the Synthesis of 2,3-Unsaturated Glycopyranosides Catalyzed by Bismuth Trichloride in Ferrier Rearrangement
  作者：N. Raghavendra Swamy、Y. Venkateswarlu

  DOI：10.1055/s-2002-23551

  日期：——

  The reaction of tri-O-acetyl-D-glucal and tri-O-benzyl-D-glucal with various alcohols and thiols to afford the corresponding glycopyranosides in excellent yields by bismuth trichloride in acetonitrile at ambient temperature has been demonstrated.

  已经证明三-O-乙酰基-D-葡糖醛和三-O-苄基-D-葡糖醛与各种醇和硫醇反应，在环境温度下通过乙腈中的三氯化铋以优异的产率提供相应的吡喃糖苷。
• ZrCl₄-Catalyzed Efficient Ferrier Glycosylation: A Facile Synthesis of Pseudoglycals
  作者：Ch. Sanjeeva Reddy、G. Smitha

  DOI：10.1055/s-2004-815974

  日期：——

  The reaction of tri-O-acetyl-d-glucal with silyl nucleophiles, alcohols and thiols was effectively promoted by a catalytic amount of zirconium(IV) chloride to produce the corresponding pseudoglycals via Ferrier rearrangement.

  三-O-乙酰基-d-葡糖醛与硅烷亲核试剂、醇和硫醇的反应在少量四氯化锆的催化作用下有效促进，生成相应的伪葡糖醛，经过Ferrier重排反应。
• Highly Diastereoselective Thioglycosylation of Functionalized Peracetylated Glycosides Catalyzed by MoO₂Cl₂
  作者：Shiue-Shien Weng、Yow-Dzer Lin、Chien-Tien Chen

  DOI：10.1021/ol062375g

  日期：2006.11.1

  Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and beta-(1 -> 6)-S-linked-thiodisaccharide synthesis.
• Ferrier Rearrangement under Nonacidic Conditions Based on Iodonium-Induced Rearrangements of Allylic n-Pentenyl Esters, n-Pentenyl Glycosides, and Phenyl Thioglycosides
  作者：J. Cristobal Lopez、Ana M. Gomez、Serafin Valverde、Bert Fraser-Reid

  DOI：10.1021/jo00117a042

  日期：1995.6
• Protic Acid (HClO₄ Supported on Silica Gel)-Mediated Synthesis of 2,3-Unsaturated-<i>O</i>-glucosides and a Chiral Furan Diol from 2,3-Glycals
  作者：Aditi Agarwal、Shikha Rani、Yashwant D. Vankar

  DOI：10.1021/jo049415j

  日期：2004.9.1

  Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good a selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl glucal with equal ease. In addition to this, a chiral furan diol is obtained from unprotected D-glucal or D-galactal in good yields.