硫代葡萄酸钠 | 62778-20-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 硫代葡萄酸钠
• 中文别名: 1-硫代-d-葡萄糖钠
• 英文名称: 1-thio-α-D-glucopyranose sodium salt
• 英文别名: alpha-D-Glucopyranose, 1-thio-, sodium salt (1:1)；sodium;(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-thiolate
• CAS: 62778-20-5
• 化学式: C₆H₁₁O₅S*Na
• 分子量: 218.206
• InChiKey: VKPBZIVFRYLHPT-WYRLRVFGSA-M

物化性质

• 熔点：
  170 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -5.66
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.2
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  硫代葡萄酸钠 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 160.0h， 生成 o-nitrophenyl 4-thio-α-maltoside
  参考文献：
  名称：

  立体选择性硫代糖苷合成。第6部分。芳基4-硫代麦芽低聚糖作为生色底物，用于α-淀粉酶的动力学研究

  摘要：

  Nucleophitic双分子取代，任一的ö -或p -硝基苯基2,3,6-三- ø -苯甲酰基-4- ö三氟甲基磺酰基α- d -galactopyranoside（1）或（2）与1钠盐在通常的脱保护序列之后，在六甲基磷酰胺中的-硫代-α- D-吡喃葡萄糖得到了邻和对硝基苯基4-硫代-α-麦芽糖苷（7）和（8）。与一个类似的合成方案（1）和4- thiomaltose（的1-α-硫醇盐12）导致Õ-硝基苯基4,4'-二硫代-α-麦芽三糖苷（15）。在比较试验中，将这些4-硫代寡糖及其相应的氧类似物用作猪和人胰腺α-淀粉酶的显色底物。在两个系列中，麦芽三糖苷衍生物的酶促速度均高于麦芽二糖。与相应的对位异构体相比，邻硝基苯基糖苷的底物性能更好。硫取代糖间氧原子会稍微提高米氏常数，但对水解速率有负面影响。因此，4-thiomaltosylpligosaccharides与他们相比有猪胰α淀粉酶

  DOI：

  10.1039/p19840001885
• 作为产物：
  描述：

  1-硫代-beta-D-葡萄糖五乙酸酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到硫代葡萄酸钠
  参考文献：
  名称：

  Synthesis of S-Linked Glycosyl Amino Acids in Aqueous Solution with Unprotected Carbohydrates

  摘要：

  [GRAPHICS]The cyclic sulfamidate 5 was synthesized in 60% overall yield from L-serine benzyl ester, Compound 5 reacted cleanly with the sodium thiolate salt of a variety of unprotected 1-thio sugars in aqueous buffer to afford the corresponding S-linked amino acid glycoconjugates in good yields after hydrolysis of the N-sulfates.

  DOI：

  10.1021/ol006908b

文献信息

• Branched thiocyclomalto-oligosaccharides: Synthesis and properties of 6-S-α- and 6-S-β-d-glucopyranosyl-6- thiocyclomaltoheptaose
  作者：Jacques Defaye、Andrée Gadelle、Alain Guiller、Raphael Darcy、Thomas O'Sullivan

  DOI：10.1016/0008-6215(89)85184-5

  日期：1989.10

  Abstract 6- S -α- ( 2 ) and 6- S -β- d -glucopyranosyl-6-thiocyclomaltoheptaose ( 3 ) have been prepared by treatment of 6- O - p -tolylsulphonylcyclomaltoheptaose ( 1 ) with the sodium salts of 1-thio-α- and -β- d -glucopyranose, respectively, in 1,3-dimethyl- 2-oxohexahydropyrimidine. Compounds 2 and 3 , which were characterised by f.a.b.-m.s. and 1 H- and 13 C-n.m.r. spectroscopy, are more soluble

  摘要用1-钠盐处理6-O-对甲苯磺酰基环麦芽庚糖（1），制备了6-S-α-（2）和6-S-β-d-吡喃葡萄糖基-6-硫代环麦芽七糖（3）。 1,3-二甲基-2-氧代六氢嘧啶中的硫代-α-和-β-d-吡喃葡萄糖。以fab-ms以及1 H-和13 Cn.mr光谱为特征的化合物2和3比环麦芽七糖更易溶于水，并通过包容增强疏水性化合物的溶解度。
• Facile synthesis of thioglucose analogs of the anticancer agent etoposide
  作者：H.D. Hollis Showalterk、R.Thomas Winters、Anthony D. Sercel、Andrè Michel

  DOI：10.1016/0040-4039(91)80629-k

  日期：1991.6

  Thioglucose-derived analogs of the clinical anticancer agent etoposide have been synthesized via a novel strategy of coupling the sugar and aglycone moieties.

  已经通过偶联糖和糖苷配基部分的新策略合成了临床抗癌剂依托泊苷的硫代葡萄糖衍生的类似物。
• Hydrogen fluoride-mediated synthesis of 1-thiotrehaloses involving reaction of d-glucose with hydrogen sulfide
  作者：Jacques Defaye、Andrée Gadelle、Christian Pedersen

  DOI：10.1016/0008-6215(91)84116-v

  日期：1991.9

  Hydrogen sulfide reacted with D-glucose in hydrogen fluoride solution to yield preponderantly alpha,alpha-1-thiotrehalose, beta,beta-1-thiotrehalose, and the alpha,beta anomer. Conditions were found under which the thiotrehaloses were obtained in the respective proportions of 8:5:5.

  硫化氢与D-葡萄糖在氟化氢溶液中反应，主要生成α，α-1-硫代海藻糖，β，β-1-硫代海藻糖和α，β异头物。发现以8：5：5的相应比例获得硫代海藻糖的条件。
• Application of Serine- and Threonine-Derived Cyclic Sulfamidates for the Preparation of <i>S</i>-Linked Glycosyl Amino Acids in Solution- and Solid-Phase Peptide Synthesis
  作者：Scott B. Cohen、Randall L. Halcomb

  DOI：10.1021/ja011932l

  日期：2002.3.1

  Cyclic sulfamidates were synthesized in 60% yield from L-serine and allo-L-threonine, respectively. These sulfamidates reacted with a variety of unprotected 1-thio sugars in aqueous bicarbonate buffer (pH 8) to afford the corresponding S-linked serine- and threonine-glycosyl amino acids with good diastereo-selectivity (greater than or equal to97%) after hydrolysis of the A sulfates. The serine-derived sulfamidate was incorporated into a simple dlipeptide to generate a reactive dipeptide substrate that underwent chemoselective ligation with a 1-thio sugar to afford an S-linked glycopeptide. This sulfamidate was also incorporated into a peptide on a solid support in conjunction with solid-phase peptide synthesis. Chemoselective ligation of a 1-thio sugar with the cyclic sulfamidate was achieved on the solid support, followed by removal of the N-sulfate. Finally, the peptide chain of the resulting support-bound S-linked glycopeptide was extended using standard peptide synthesis procedures.
• Blanc-Muesser, Michele; Defaye, Jacques; Driguez, Hugues, Journal of the Chemical Society. Perkin transactions I, 1982, p. 15 - 18
  作者：Blanc-Muesser, Michele、Defaye, Jacques、Driguez, Hugues

  DOI：——

  日期：——