1-deoxy-1-thio-α-D-glucopyranose | 63073-99-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-1-thio-α-D-glucopyranose
• 英文别名: 1-deoxy-1-thio-α-D-glucose；1-thio-α-D-glucopyranose；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triol；β-D-thioglucose；α-D-1-thio-glucopyranose；1-thio-α-D-glucose；α-thioglucose；1-Thio-alpha-D-glucopyranose；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-sulfanyloxane-3,4,5-triol
• CAS: 63073-99-4
• 化学式: C₆H₁₂O₅S
• 分子量: 196.224
• InChiKey: JUSMHIGDXPKSID-VFUOTHLCSA-N

物化性质

• 熔点：
  119 °C
• 沸点：
  432.6±45.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 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：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-thio-α-D-glucopyranose 在 吡啶 、 三乙基硅烷 、 水 、 sodium methylate 、 四丁基硫酸氢铵 、 碳酸氢钠 、 三氟乙酸 、 sodium iodide 、 sodium thiomethoxide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 77.0h， 生成 4′-monomethoxytrityl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranosyl-S-(1→6)-2,3,4-tri-O-acetyl-1-thio-α-D-glucopyranosyl-S-(1→6)-2,3,4-tri-O-acetyl-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Expedient synthesis of an α-S-(1→6)-linked pentaglucosyl thiol

  摘要：

  通过最长的线性序列，从α-葡萄糖硫醇（7）合成了一种α-S-(1→6)-连接的五聚葡萄糖硫醇（1），共进行了十一个步骤。

  DOI：

  10.1039/c4ob01094a
• 作为产物：
  描述：

  sodium 1-thio-β-D-glucopyranoside 生成 1-deoxy-1-thio-α-D-glucopyranose
  参考文献：
  名称：

  pH-Dependent Mutarotation of 1-Thioaldoses in Water. Unexpected Behavior of (2S)-d-Aldopyranoses

  摘要：

  The pH-dependent mutarotation of 1-thioaldopyranoses in aqueous media has been investigated. Anomerization readily occurred at lower and neutral pH for all aldopyranoses studied, whereas mainly for (2S)-D-aldopyranoses at higher pH. 1-Thio-D-mannopyranose and 1-thio-D-altropyranose showed very strong pH dependence where the anomeric equilibrium ratios changed dramatically from a preference for the beta-anomer at lower pH to the alpha-anomer at higher pH.

  DOI：

  10.1021/jo100826e

文献信息

• Thiyl Glycosylation of Olefinic Proteins: S-Linked Glycoconjugate Synthesis
  作者：Nicola Floyd、Balakumar Vijayakrishnan、Julia R. Koeppe、Benjamin G. Davis

  DOI：10.1002/anie.200903135

  日期：2009.10.5

  (homoallylglycine, Hag) as a “tag” for modification and a photoinitiated hydroglycothiolation reaction that is selective only for the Hag olefinic “tag”. Application of this method to a number of model proteins allowed complete and precise site‐selective glycosylation generating glycoconjugates that include, for example, virus‐like particles displaying up to 180 glycans at preselected positions (see scheme).

  标记为硫醇化：一种新的糖缀合策略利用非天然含烯烃的氨基酸（高烯丙基甘氨酸，Hag）作为修饰的“标签”和仅对 Hag 烯烃“标签”有选择性的光引发氢糖硫醇化反应。将此方法应用于许多模型蛋白，可以实现完整和精确的位点选择性糖基化生成糖缀合物，例如，在预选位置显示多达 180 个聚糖的病毒样颗粒（参见方案）。
• Stereoretentive Palladium-Catalyzed Arylation, Alkenylation, and Alkynylation of 1-Thiosugars and Thiols Using Aminobiphenyl Palladacycle Precatalyst at Room Temperature
  作者：Alexandre Bruneau、Maxime Roche、Abdallah Hamze、Jean-Daniel Brion、Mouad Alami、Samir Messaoudi

  DOI：10.1002/chem.201501050

  日期：2015.6.1

  A general and efficient protocol for the palladium‐catalyzed functionalization of mono‐ and polyglycosyl thiols by using the palladacycle precatalyst G3‐XantPhos was developed. The CS bond‐forming reaction was achieved rapidly at room temperature with various functionalized (hetero)aryl‐, alkenyl‐, and alkynyl halides. The functional group tolerance on the electrophilic partner is typically high and

  通过使用Palladacycle预催化剂G3-XantPhos，开发了一种通用且有效的协议，用于钯催化的单糖基和聚糖基硫醇官能化。与c  S键形成反应，在室温下用各种官能化（杂）芳基- ，链烯基，和炔基卤化物快速地实现。在所研究的所有情况下，对亲电子体的官能团耐受性通常都很高，并且硫代糖苷的端基异构体选择性也很高。新的硫亲核试剂，如硫酚，烷基硫醇和硫代氨基酸（半胱氨酸）也已成功偶联，从而导致了迄今报道的最通用和最实用的硫醇官能化方法。
• α-(1 → 2)-, α-(1 → 3)-, and α-(1 → 6)-Linked thioglycosidic disaccharides: syntheses and anti-HIV testing of thiokojibiose octaacetate, thionigerose, and thioisomaltose
  作者：Robert N. Comber、Joyce D. Friedrich、David A. Dunshee、Sandra L. Petty、John A. Secrist

  DOI：10.1016/0008-6215(94)84182-9

  日期：1994.9

  3-O-trifluoromethylsulfonyl-alpha-D-++ +allofuranose (15), or methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-alpha-D-glucopyranoside (17), respectively. Thiokojibiose octaacetate in turn was converted to 3,4,6-tri-O-acetyl-2-S-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-2 -thio-alpha-D-glucopyranosyl bromide (9), which was used to obtain several related disaccharides and one trisaccharide. All of the

  描述了几种α-连接的硫糖苷二糖的合成，包括巯基二糖八乙酸酯（1），硫代黑糖（2）和硫代异麦芽糖（3）。通过将2,3,4,6-四-O-乙酰基-1.5-乙酰基-1-硫代-α-D-吡喃葡萄糖（4）与1,3,4,6-四-O偶合来合成标题化合物-乙酰基-2-O-三氟甲基磺酰基-β-D-甘露糖吡喃糖（7），1,2：5,6-二-O-异亚丙基-3-O-三氟甲基磺酰基-α-D-++ +铝呋喃糖（15 ）或甲基2,3,4-三-O-乙酰基-6-脱氧-6-碘-α-D-吡喃葡萄糖苷（17）。硫代oji二糖八乙酸酯依次转化为3,4,6-三-O-乙酰基-2-S-（2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基）-2-硫代-α -D-吡喃葡萄糖基溴化物（9），用于获得几种相关的二糖和一种三糖。所有化合物，包括硫代麦芽糖和硫代海藻糖，通过已知方法重新合成的它们在CEM或MT-2细胞中测试其抗HIV活性。仅使用硫代曲霉
• Nickel-Catalyzed Arylation, Alkenylation, and Alkynylation of Unprotected Thioglycosides at Room Temperature
  作者：Etienne Brachet、Jean-Daniel Brion、Mouad Alami、Samir Messaoudi

  DOI：10.1002/chem.201302999

  日期：2013.11.4

  Unprotected thioglycosides were effective nucleophiles for Ni0‐catalyzed CS bond‐forming reaction with functionalized (hetero)aryl, alkenyl, and alkynyl halides. The functional‐group tolerance on the electrophilic partner was typically high and the anomeric selectivities of the thioglycosides were high in all cases. The efficiency of this general procedure was well‐demonstrated by the synthesis of

  未保护的硫代糖苷是Ni 0催化的CS键与官能化的（杂）芳基，烯基和炔基卤化物反应的有效亲核试剂。在所有情况下，对亲电子分子的官能团耐受性通常都很高，硫代糖苷的端基异构体选择性也很高。合成4-甲基-7-硫代伞形酮基-β- D-纤维二糖苷（MUS-CB）很好地证明了这种通用程序的效率。
• One-pot synthesis of hyperbranched poly(amido amine) clicked with a sugar shell via Michael addition polymerization and thiol click reaction
  作者：ZhiQiang Yu、MengMeng Cui、JunJie Yan、YeZi You

  DOI：10.1007/s11426-010-4050-8

  日期：2010.8

  This paper reports the production of glycopolymers via a simple and flexible method. A novel glycopolymer with a hyperbranched poly(amido amine) core and a sugar shell (HPAA-GLc) was synthesized by using thiol-ene click reaction via facile one-pot method. Hyperbranched poly(amido amine) with vinyl terminals was first synthesized by Michael addition polymerization of N,N′-methylene bisacrylamide (MBA)

  本文报道了通过简单灵活的方法生产糖聚合物的方法。通过硫醇-烯点击反应，通过简便的一锅法合成了具有超支化聚（酰胺胺）核和糖壳的新型糖聚合物（HPAA-GLc）。首先通过N，N′-亚甲基双丙烯酰胺（MBA）与1-（2-氨基乙基）哌嗪（AEPZ）的迈克尔加成聚合反应合成具有乙烯基端基的超支化聚（酰胺基胺）。随后，在原位进行超支化聚（酰胺基胺）的乙烯基单元和硫代葡萄糖之间的硫醇-烯点击反应。基于NMR结果，所有乙烯基在120分钟内与硫醇-葡萄糖反应。从HPAA-GLc的水溶液观察到强的光致发光发射。