phenyl 2,3,6-trideoxy-1-thio-α-D-threo-hex-2-enopyranoside | 135726-16-8

• 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 2,3,6-trideoxy-1-thio-α-D-threo-hex-2-enopyranoside
• 英文别名: (2R,3R,6R)-2-methyl-6-phenylsulfanyl-3,6-dihydro-2H-pyran-3-ol
• CAS: 135726-16-8
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: QJRCFYFBAMIKHS-YUSALJHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,6-trideoxy-1-thio-α-D-threo-hex-2-enopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 3-羧基苯甲醛 、 三苯基膦氢溴酸盐 、 sodium hydride 、 sodium cyanoborohydride 、 potassium carbonate 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二乙胺 、 三乙胺 、 乙硫醇 、 肼 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 2.0h， 生成 (4-methoxyphenyl)methyl 4,6-dideoxy-4-<<2,4,6-trideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-(methylthio-β-D-ribo-hexopyranosyl)oxy><2-(trimethylsilyl)ethoxycarbonyl>amino>-2-O-<2,4-dideoxy-3-O-methyl-4-<(1-methylethyl)amino>-α-L-threo-pentopyra>..
  参考文献：
  名称：

  Observations in the Chemistry and Biology of Cyclic Enediyne Antibiotics:  Total Syntheses of Calicheamicin γ₁^I and Dynemicin A

  摘要：

  DOI：

  10.1021/jo951560x
• 作为产物：
  描述：

  D-三乙酰半乳糖烯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 phenyl 2,3,6-trideoxy-1-thio-α-D-threo-hex-2-enopyranoside
  参考文献：
  名称：

  Total Synthesis of (+)-Pyrenolide D

  摘要：

  DOI：

  10.1002/1521-3773(20010316)40:6<1128::aid-anie11280>3.0.co;2-j

文献信息

• Studies Toward the Total Synthesis of Pluraflavin A
  作者：John Hartung、Benjamin J. D. Wright、Samuel J. Danishefsky

  DOI：10.1002/chem.201402254

  日期：2014.7.7

  core bearing a halogen atom enabled the introduction of the α C‐aryl glycoside by Stille cross‐coupling and subsequent hydrogenation of the aryl glycal. Chemo‐ and stereoselective O‐glycosylations of α oliose and β 3‐epi vancosamine residues afforded a fully glycosylated aromatic core. Attempts to install the dimethylamino group of the C‐disaccharide suggest that introduction of an azide group by displacement

  已经开发了一种针对强效细胞抑制剂 pluraflavin A 的合成策略。带有卤素原子的对映体富集的蒽吡喃核心的形成使得 α C-芳基糖苷的引入能够通过 Stille 交叉偶联和随后的芳基糖基化。α oliose 和 β 3-epi 万考胺残基的化学和立体选择性 O-糖基化提供了完全糖基化的芳香族核心。安装 C-二糖的二甲基氨基的尝试表明，通过置换和随后的还原引入叠氮化物基团可能为多黄素 A 的完全合成铺平道路。
• Stereoselective Synthesis of α-Digitoxosides and α-Boivinosides via Chelation-Controlled Anomeric<i>O</i>-Alkylation
  作者：Danyang Zhu、Surya Adhikari、Kedar N. Baryal、Belal N. Abdullah、Jianglong Zhu

  DOI：10.1080/07328303.2014.931965

  日期：2014.10.13

  A chelation-controlled anomeric O-alkylation has been developed for the stereoselective synthesis of α-digitoxosides and α-boivinosides bearing a C3-free hydroxyl group. Due to chelation via sodium ion, the anomeric alkoxides are locked in the axial configuration, which leads to the selective production of α-glycosides.

  已经开发了螯合控制的异头O-烷基化反应，用于立体选择性地合成α-数字氧苷和带有C3-游离羟基的α-boivinosides。由于经由钠离子的螯合，异头醇盐被锁定在轴向构型中，这导致选择性产生α-糖苷。
• The synthesis of the core trisaccharide of esperamicin: corroboration of the proposed structure for its rearrangement product and stabilization of the core trisaccharide domain
  作者：Randall L. Halcomb、Mark D. Wittman、Steven H. Olson、Samuel J. Danishefsky、Jerzy Golik、Henry Wong、Dolatrai Vyas

  DOI：10.1021/ja00013a065

  日期：1991.6
• Studies Related to the Carbohydrate Sectors of Esperamicin and Calicheamicin: Definition of the Stability Limits of the Esperamicin Domain and Fashioning of a Glycosyl Donor from the Calicheamicin Domain
  作者：Randall L. Halcomb、Serge H. Boyer、Mark D. Wittman、Steven H. Olson、Derek J. Denhart、Kevin K. C. Liu、Samuel J. Danishefsky

  DOI：10.1021/ja00126a013

  日期：1995.5

  The core trisaccharide regions of esperamicin and the aryltetrasaccharide region of calicheamicin have been synthesized. The minimum protection modalities necessary to stabilize structures against rearrangement to an isomeric azafuranose series were ascertained (see compounds 12 and 65). Deprotection of the 2-(trimethylsilyl)ethoxycarbonyl carbamate from 65 led to azafuranose 14 characterized as methyl glycoside 15. Using this insight, it was possible to fashion, for the first time, a pre-glycosyl donor (see compound 128) corresponding to the complete arylsaccharide sector of calicheamicin gamma(1)(I) at the oxidation level of the domain. Among the key assembly strategies were the conversion of alpha-thiophenylpseudoglycals to allal derivatives (see 44 --> 45); the interfacing of epoxide-mediated glycosylation with iodoglycosylation (see 30 --> 47 --> 48); the synthesis of hydroxylamine glycosides via triflate displacement (see 61 + 91 --> 101); and a new route to p-hydroxybenzonitriles (see formation of 86).
• HALCOMB, RANDALL L.;WITTMAN, MARK D.;OLSON, STEVEN H.;DANISHETSKY, SAMUEL+, J. AMER. CHEM. SOC., 113,(1991) N3, C. 5080-5082
  作者：HALCOMB, RANDALL L.、WITTMAN, MARK D.、OLSON, STEVEN H.、DANISHETSKY, SAMUEL+

  DOI：——

  日期：——