methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside | 114217-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside
• 英文别名: 1-O-methyl-3,4-O-acetonide-6-OTBDPS-α-D-galactopyranose；(3aS,4R,6S,7R,7aR)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 114217-36-6
• 化学式: C₂₆H₃₆O₆Si
• 分子量: 472.654
• InChiKey: HNLVRGKVSUNDEF-SJSRKZJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 anti,syn-anti-2,5-bis(hydroxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran
  参考文献：
  名称：

  用于立体定向合成α-和β-C-核苷的中间体的合成：半乳糖和吡喃葡糖苷的受保护2-0-三氟甲磺酸盐的环收缩

  摘要：

  叠氮化钠与甲基6-0-（-丁基二苯基）甲硅烷基-3,4-0-异亚丙基-2-0-三氟甲磺酰基-D-吡喃半乳糖苷与甲基6-0-（-丁基二苯基）甲硅烷基-3,4的反应-0-异亚丙基-2-0-三氟甲烷-磺酰基-α-D-阿托吡喃糖苷分别提供适合于立体定向合成α-和β-C-核苷的中间体。

  DOI：

  10.1016/s0040-4039(00)96272-5
• 作为产物：
  描述：

  (2R,3R,4R,5R,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-methoxyoxane-3,4,5-triol 、 2,2-二甲氧基丙烷 生成 methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside
  参考文献：
  名称：

  KNAPP, SPENCER;KUKKOLA, PAIVI J., J. ORG. CHEM., 55,(1990) N, C. 1632-1636

  摘要：

  DOI：

文献信息

• Synthesis of specifically deoxygenated disaccharide derivatives of the Shigella dysenteriae type 1 O-antigen
  作者：Laurence A. Mulard、Cornelis P.J. Claudemans

  DOI：10.1016/0008-6215(95)00122-a

  日期：1995.9

  The synthesis of methyl O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-D-galactopyranosides specifically deoxygenated at position 2 (31), or 4 (21) of the rhamnopyranosyl residue was accomplished using methyl 3,4,6-tri-O-benzoyl-alpha-D-galactopyranoside (18) as the glycosyl acceptor. Phenyl thionocarbonate activation of the penta-O-benzoylated disaccharide precursor followed by Barton reduction and Zemplén

  使用3,4甲基合成在鼠李糖吡喃糖基残基的位置2（31）或4（21）上特别脱氧的甲基O-α-L-鼠李糖吡喃糖基-（1→2）-α-D-吡喃半乳糖苷，6-三-O-苯甲酰基-α-D-吡喃半乳糖苷（18）作为糖基受体。五-O-苯甲酰化二糖前体的苯硫代碳酸酯活化，然后进行Barton还原和Zemplén酯交换，得到31，而通过脱氧单糖供体与18的缩合反应以及随后产物的脱苯甲酰化，得到21。
• Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors
  作者：Andrew B. Mayfield、Jan B. Metternich、Adam H. Trotta、Eric N. Jacobsen

  DOI：10.1021/jacs.0c00335

  日期：2020.2.26

  We report a new method for stereoselective O-furanosylation reactions promoted by a precisely tailored bis-thiourea hydrogen-bond-donor catalyst. Furanosyl donors outfitted with an anomeric dialkylphosphate leaving group undergo substitution with high anomeric selectivity, providing access to the challenging 1,2-cis substitution pattern with a range of alcohol acceptors. A variety of stereochemically distinct, benzyl-protected glycosyl donors were engaged successfully as substrates. Mechanistic studies support a stereospecific mechanism in which rate-determining substitution occurs from a catalyst-donor resting-state complex.
• Amine-free silylation of alcohols under 4-methylpyridine N-oxide-catalyzed conditions
  作者：Keisuke Yoshida、Yuta Fujino、Yukihiro Itatsu、Hiroki Inoue、Yohei Kanoko、Ken-ichi Takao

  DOI：10.1016/j.tetlet.2015.12.114

  日期：2016.2

  Amine-free silylation of various alcohols catalyzed by 4-methylpyridine N-oxide in the presence of MS4A at room temperature was developed. This simple method gave various silyl ethers in a high yield. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of Disaccharides Related to the O-Specific Side Chains from <i>E.coli</i> O126 &amp; O128 Lipopolysaccharides
  作者：Prabal Sengupta、Sumita Sarbajna、Sumanta Basu

  DOI：10.1080/07328309908543981

  日期：1999.1.1

  Starting from D-galactose and L-fucose, four disaccharides, namely methyl beta-L-fucopyranosyl-(1-->2)-alpha-D-galactopyranoside, methyl alpha-1-fucopyranosyl-(1-->2)-alpha-D-galactopyranoside, methyl alpha-L-fucopyranosyl-(1-->2)-beta-D-galactopyranoside and methyl beta-L-fucopyranosyl-(1-->2)-beta-D-galactopyranoside related to the repeating units of E.coli O126 and O128 have been synthesized using NIS and TfOH as promoter.
• Synthesis of a disaccharide fragment of rhamnogalacturonan II
  作者：Magali A.J. Buffet、Jamie R. Rich、Robert S. McGavin、Kerry B. Reimer

  DOI：10.1016/j.carres.2004.08.004

  日期：2004.10

  A disaccharide portion of the A-side chain of the rhamnogalacturonan II oligosaccharide has been prepared. Glycosylation of methyl (methyl 3,4-O-isopropylidene-alpha-D-galactopyranosid)uronate with p-tolyl 2,3-di-O-acetyl-3-C-(benzyloxymethyl)-1-thio-alpha/beta-D-erythrofuranoside was carried out using N-iodosuccinimide as promoter and silver trifluoromethanesulfonate as catalyst. Removal of the protecting groups gave the beta-D-Apif-(1-->2)-alpha-D-GalpA-OMe disaccharide. (C) 2004 Elsevier Ltd. All rights reserved.