3,4-di-O-benzyl-1,2:5,6-di-O-sulfenyl-D-mannitol | 151477-85-9

• 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: 3,4-di-O-benzyl-1,2:5,6-di-O-sulfenyl-D-mannitol
• 英文别名: (4R)-4-[(1S,2S)-2-[(4R)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-1,2-bis(phenylmethoxy)ethyl]-1,3,2-dioxathiolane 2,2-dioxide
• CAS: 151477-85-9
• 化学式: C₂₀H₂₂O₁₀S₂
• 分子量: 486.521
• InChiKey: SCQLJMOMCWFUFL-UAFMIMERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzyl-1,2:5,6-di-O-sulfenyl-D-mannitol 在 4-二甲氨基吡啶 、 叠氮化锂 、 硫酸 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-tert-butoxycarbonyl)-aziridine
  参考文献：
  名称：

  Yokomatsu, Tsutomu; Suemune, Kenji; Shibuya, Shiroshi, Heterocycles, 1993, vol. 35, # 2, p. 577 - 580

  摘要：

  DOI：
• 作为产物：
  描述：

  双丙酮-D-甘露糖醇 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 sodium hydride 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,4-di-O-benzyl-1,2:5,6-di-O-sulfenyl-D-mannitol
  参考文献：
  名称：

  Yokomatsu, Tsutomu; Suemune, Kenji; Shibuya, Shiroshi, Heterocycles, 1993, vol. 35, # 2, p. 577 - 580

  摘要：

  DOI：

文献信息

• Applications of Cyclic Sulfates of <i>vic</i>-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars
  作者：Francisco G. Calvo-Flores、Pilar García-Mendoza、Fernando Hernández-Mateo、Joaquín Isac-García、Francisco Santoyo-González

  DOI：10.1021/jo962066b

  日期：1997.6.13

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.
• Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives. Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration
  作者：Virginie Glaçon、Mohammed Benazza、Daniel Beaupère、Gilles Demailly

  DOI：10.1016/s0040-4039(00)00791-7

  日期：2000.6

  The bis-cyclic sulfate derivatives of erythritol (1), D,L-threitol (5), 3,4-di-O-benzyl-D-mannitol (9), 1,2-O-isopropylidene-D-mannitol (14) and 1-O-benzyl-D,L-xylitol (18) were submitted to nucleophilic attack by allylamine or sodium sulfide. In both cases, heterocyclisation occurred and aza or thioanhydrodeoxyalditols were obtained in moderate to good yields (40 to 89%). With compound 9, 1,5-anhydro-5-thio-L-gulitol (12) was obtained as the main product, a result that is in contrast with previous results reported in the literature using bis-epoxide as bielectrophile intermediate.(1) (C) 2000 Published by Elsevier Science Ltd.
• Yokomatsu, Tsutomu; Suemune, Kenji; Shibuya, Shiroshi, Heterocycles, 1993, vol. 35, # 2, p. 577 - 580
  作者：Yokomatsu, Tsutomu、Suemune, Kenji、Shibuya, Shiroshi

  DOI：——

  日期：——