phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-sulfonyl-α-D-erythro-hex-2-enopyranoside | 125472-23-3

• 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: phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-sulfonyl-α-D-erythro-hex-2-enopyranoside
• 英文别名: (2R,3S,6R)-3-acetoxy-6-(benzenesulphonyl)-3,6-dihydro-2H-pyran-2-methanol acetate；(2R,3S,6R)-3-acetoxy-3,6-dihydro-6-(phenylsulphonyl)-2H-pyran-2-methanol acetate；[(2R,3S,6R)-3-acetyloxy-6-(benzenesulfonyl)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 125472-23-3
• 化学式: C₁₆H₁₈O₇S
• 分子量: 354.381
• InChiKey: FXLHWGQFZYFOKF-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 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：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-sulfonyl-α-D-erythro-hex-2-enopyranoside 在 ruthenium trichloride 、 sodium periodate 、 水 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 0.5h， 以92%的产率得到C₁₆H₂₀O₉S
  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：

  苯硫酚 在 ruthenium trichloride 、 sodium periodate 、 phenyl 2,3,4-tri-O-acetyl-1-thio-D-mannopyranose 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 0.33h， 生成 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-sulfonyl-α-D-erythro-hex-2-enopyranoside
  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

文献信息

• Use of 2-phenylsulphonyl cyclic ethers in the preparation of tetrahydropyran and tetrahydrofuran acetals and in some glycosidation reactions.
  作者：Dearg S. Brown、Steven V. Ley、Sadie Vile、Mervyn Thompson

  DOI：10.1016/s0040-4020(01)86389-4

  日期：1991.1

  2-Phenylsulphonyl cyclic ethers undergo facile displacement of the sulphonyl group by alcohols, in the presence of magnesium bromide etherate and sodium bicarbonate in tetrahydrofuran, to give goodyields of the corresponding acetals.

  2-苯基磺酰基环醚在四氢呋喃中的溴化镁醚化物和碳酸氢钠存在下，通过醇容易地置换磺酰基，以得到相应的缩醛的良好收率。
• Substitution reactions of 2-benzenesulphonyl cyclic ethers with carbon nucleophiles
  作者：Dearg S. Brown、Maurizio Bruno、Raymond J. Davenport、Steven V. Ley

  DOI：10.1016/s0040-4020(01)81323-5

  日期：1989.1

  Direct substitution of 2-benzenesulphonyl cyclic ethers was studied using a variety of carbon nucleophiles. These nucleophiles included organozinc reagents (derived from aryl, vinyl and alkynyl Grignard reagents) or silyl enol ethers, silyl ketene acetals, allylsilanes and trimethylsilylcyanide in the presence of aluminum chloride. A general selectivity for the formation of the trans-product was observed

  使用多种碳亲核试剂研究了2-苯磺酰基环醚的直接取代。这些亲核试剂包括有机锌试剂（衍生自芳基，乙烯基和炔基格利雅试剂）或甲硅烷基烯醇醚，甲硅烷基乙烯酮缩醛，烯丙基硅烷和三甲基甲硅烷基氰化物。使用6-取代的砜观察到形成反式产物的一般选择性。
• Addition Reactions of Benzenesulfinic Acid with Glycals and 1,2-Dibromosugars
  作者：Vikram Basava、Broc Flores、Matthew Giovine、Thomas Licisyn、Katelyn Walck、Walter Boyko、Robert Giuliano

  DOI：10.1080/07328300802374805

  日期：2008.10.30

  under various conditions, and optimized yields of the glycosyl phenylsulfone products were obtained in the presence of tin tetrachloride as a catalyst. Double bond shift (Ferrier rearrangement) occurred in all cases except amicetal, which lacks a substituent at the allylic carbon. Glycosylation of benzenesulfinic acid with 1,2-dibromides was carried out using silver triflate as the promoter, and gave

  在各种条件下研究了将苯亚磺酸加到缩醛中，并在四氯化锡作为催化剂存在下获得了最佳的糖基苯基砜产物收率。除amicetal以外，所有情况均发生双键移位（Ferrier重排），而amicetal在烯丙基碳上缺少取代基。使用三氟甲磺酸银作为促进剂，用1,2-二溴化物对苯磺酸进行糖基化，通过在氧气而不是硫的反应下得到亚磺酸酯作为产物。以立体异构体在立体硫原子上的混合物形式获得亚磺酸酯。在尝试用MCPBA氧化的过程中，观察到亚磺酸盐被羧酸盐亲核试剂捕获。
• Braithwaite, Dana H.; Holzapfel, Cedric W.; Williams, D. Bradley G., South African Journal of Chemistry, 1998, vol. 51, # 4, p. 162 - 164
  作者：Braithwaite, Dana H.、Holzapfel, Cedric W.、Williams, D. Bradley G.

  DOI：——

  日期：——
• BROWN, DEARG S.;LEY, STEVEN V.;VILE, SADIE, TETRAHEDRON LETT., 29,(1988) N 38, C. 4873-4876
  作者：BROWN, DEARG S.、LEY, STEVEN V.、VILE, SADIE

  DOI：——

  日期：——