1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (-)-(SS)-methane-sulfinate | 138665-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (-)-(SS)-methane-sulfinate
• 英文别名: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl-(-)-(SS)-methane-sulfinate；(SS)-MeSO2-DAG；[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methanesulfinate
• CAS: 138665-21-1
• 化学式: C₁₃H₂₂O₇S
• 分子量: 322.379
• InChiKey: UOAQMPDRBKTTFV-QHTMXPIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-dihydronaphthalen-1(2H)-one O-methyl oxime 、 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (-)-(SS)-methane-sulfinate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.75h， 以1.43 g的产率得到2-(methylsulfinyl)-3,4-dihydronaphthalen-1(2H)-one O-methyl oxime
  参考文献：
  名称：

  Insights for diastereoselective synthesis of cyclic α-sulfinyl and sulfanyl oximes

  摘要：

  The comparison in several reaction conditions for synthesis of nonracemic alpha-methylsulfinylation of 3,4-dihydronaphthalen-1(2H)-one was achieved. The sulfanylation reactions of 3,4-dihydronaphthalen-1 (2H)-one-O-methyloxime and 2-(methylsulfinyl)-3,4-dihydronaphthalen-1(2H)-one-O-methyloxime by homogenous reaction medium are reported. The products were obtained in good yields and de. The yields, diastereoselectivity and theoretical calculations to all obtained compounds to support the experimental data are compared and discussed. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.04.083
• 作为产物：
  描述：

  甲烷磺酰基氰化物 、 双丙酮葡萄糖 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (-)-(SS)-methane-sulfinate
  参考文献：
  名称：

  O-sulfinylation with methanesulfonyl cyanide or p-toluenesulfonyl cyanide and DBU.

  摘要：

  Reaction of methanesulfonyl cyanide or p-toluenesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates is suggested.

  DOI：

  10.1016/s0040-4039(00)78791-0

文献信息

• Asymmetric phase-transfer catalytic sulfanylation of some 2-methylsulfinyl cyclanones. Modeling of the stereochemical course of the aldol reaction of (SS,2S)-2-methylsulfinyl-2-methylsulfanylcyclohexanone
  作者：Alessandro Rodrigues、Blanka Wladislaw、Claudio Di Vitta、José Eduardo Pandini Cardoso Filho、Liliana Marzorati、Mauro Alves Bueno、Paulo Roberto Olivato

  DOI：10.1016/j.tetlet.2010.08.010

  日期：2010.10

  2-methylsulfinyl cyclanones under phase-transfer catalysis using the chiral catalyst QUIBEC instead of TEBA. The optically pure (SS,2S)-2-methylsulfinyl-2-methylsulfanylcyclohexanone thus prepared reacts with ethyl acetate lithium enolate affording, after hydrolysis, (R)-2-[(ethoxycarbonyl)methyl]-2-hydroxycyclohexanone in 60% ee. Density functional theory calculations (at the B3LYP/6-311++G(d,p) level)

  使用手性催化剂QUIBEC代替TEBA，在相转移催化下，某些2-甲基亚磺酰基环戊酮的磺酰化反应会增加非对映异构体过量。如此制备的光学纯的（S S，2 S）-2-甲基亚磺酰基-2-甲基硫烷基环己酮与乙酸乙酯烯醇锂反应，水解后得到60％的（R）-2-[（乙氧基羰基）甲基] -2-羟基环己酮ee。密度泛函理论计算（在B3LYP / 6-311 ++ G（d，p）水平）可以成功地解释此结果的起源，因为亲核试剂对分子中最稳定构象异构体的羰基具有动力学上的轴向攻击。环烷酮，其中CH 3 SO和CH 3S组分别位于赤道和轴向位置。
• O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide.
  作者：Derek H.R. Barton、Joseph Cs. Jaszberenyi、Emmanouil A. Theodorakis

  DOI：10.1016/s0040-4020(01)96204-0

  日期：1991.11

  Reaction of p-toluenesulfonyl cyanide or methanesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates 9 and 21 is suggested.