(2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6- propyltetrahydro-2H-pyran-3,4,5-triol | 110352-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6- propyltetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6-propyloxane-3,4,5-triol
• CAS: 110352-30-2
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: PNQDGCOQVLHKHH-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6- propyltetrahydro-2H-pyran-3,4,5-triol 在 盐酸 、 3 A molecular sieve 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.5h， 生成 1-(2,3-di-O-benzyl-α-D-glucopyranosyl)propane
  参考文献：
  名称：

  Multifunctionalized α,β-cyclopentenones from C-2 and C-4-ulopyranosyl compounds: a stereospecific rearrangement initiated by base

  摘要：

  Base treatment of O-benzyl protected C-2- or C-4-ulopyranosyl compounds (4 alpha, 4 beta, and 11) by either 10% Et3N or 1% K2CO3 in MeOH initiated a beta elimination to afford alpha,beta-unsaturated C-ulopyranosyl compounds (5 alpha, 5 beta, and 12), which further rearranged in a stereocontrolled manner to multifuctionalized alpha,beta-cyclopentenones (6 and 14) in 70-80% yield. Both C-alpha- and C-beta-2-ulosides (5 alpha and 5 beta) produced the same cyclopentenone 6, indicating that a 1,2-enolate is formed prior to the cleavage of the C-5-O bond. Because 6 is racemic, it was probably formed by the intramolecular cycloaldolization of two equally populated enantiomeric intermediates. When treated with 90% Et3N in MeOH, 5 alpha yielded almost exclusively 15 (isomer of 6), which was formed by a migration of the double bond in 5 alpha during the previously described rearrangement. Thus either 6 or 15 was the major product, depending on the base used. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00187-2
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-propene 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 8.0h， 生成 (2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6- propyltetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  对映体纯的α，β-不饱和五元环醛通过环氧己吡喃糖苷的环收缩而形成。

  摘要：

  一系列在6位上被不同取代的环氧己吡喃糖苷各自通过环收缩而转变成单个对映体纯的α，β-不饱和呋喃硅醛。环氧己吡喃糖苷之一的C-丙基糖苷类似物的类似的环收缩产生了两种非对映异构醛的混合物。该发现支持了先前提出的反应机理，并表明O-糖苷型环氧吡喃糖苷也重排成两个醛，其中之一是不稳定的。

  DOI：

  10.1021/jo970666k

文献信息

• Preferred conformation of C-glycosides. 6. Conformational similarity of glycosides and corresponding C-glycosides
  作者：Peter G. Goekjian、Tse Chong Wu、Yoshito Kishi

  DOI：10.1021/jo00022a038

  日期：1991.10

  The conformation of the alpha-(axial)-C-glycosides 1-3 and the beta-(equatorial)-C-glycosides 4-6 were studied by H-1 NMR. Their preferred solution conformation was found to match that of the corresponding parent glycosides. The study of 2-deoxy compounds 13-16 shows that the preference is due primarily to gauche interactions around the glycosidic bond. Solvent studies indicate that electrostatic interactions and hydrogen bonds do not significantly alter the overall conformation. Temperature studies suggest that these compounds exist as an equilibrium mixture of conformers.
• Operationally Simple and Efficient Workup Procedure for TBAF-Mediated Desilylation:  Application to Halichondrin Synthesis
  作者：Yosuke Kaburagi、Yoshito Kishi

  DOI：10.1021/ol063113h

  日期：2007.2.1

  An operationally simple and efficient workup method for tetrabutylammonium fluoride (TBAF)-mediated t-butyldimethylsilyl (TBS) deprotection has been developed. The procedure includes addition of a sulfonic acid resin and calcium carbonate, followed by filtration and evaporation. This method eliminates the tedious aqueous-phase extraction process to remove excess TBAF and materials derived from TBAF, thereby making the protocol highly amenable to multiple TBS deprotections. Its efficiency and usefulness were demonstrated by using the transformation of 1a to 3a in the halichondrin synthesis.
• [EN] C-GLYCOSIDES AS ANTI-INFLAMMATORY AGENTS<br/>[FR] C-GLYCOSIDES UTILISÉS COMME AGENTS ANTI-INFLAMMATOIRES
  申请人：[en]UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：WO2024010959A1

  公开（公告）日：2024-01-11

  Novel compounds and methods of using the compounds are provided herein. The compounds include novel carbon analogs of pyranose derivatives discovered to have Toll- like receptor 4 (Tlr4) inhibitory activity. The methods provide for treating infectious, inflammatory and post-traumatic disorders.
• Enantiomerically Pure α,β-Unsaturated Five-Membered-Ring Aldehydes by Ring Contraction of Epoxyhexopyranosides
  作者：Fritiof Pontén、Göran Magnusson

  DOI：10.1021/jo970666k

  日期：1997.11.1

  single, enantiomerically pure, alpha,beta-unsaturated furanosidic aldehyde. Similar ring contraction of a C-propylglycosidic analog of one of the epoxyhexopyranosides gave a mixture of two diastereomeric aldehydes. This finding supports the previously suggested mechanism of the reaction and indicates that O-glycosidic epoxypyranosides also rearrange into two aldehydes, one of which is unstable.

  一系列在6位上被不同取代的环氧己吡喃糖苷各自通过环收缩而转变成单个对映体纯的α，β-不饱和呋喃硅醛。环氧己吡喃糖苷之一的C-丙基糖苷类似物的类似的环收缩产生了两种非对映异构醛的混合物。该发现支持了先前提出的反应机理，并表明O-糖苷型环氧吡喃糖苷也重排成两个醛，其中之一是不稳定的。
• Multifunctionalized α,β-cyclopentenones from C-2 and C-4-ulopyranosyl compounds: a stereospecific rearrangement initiated by base
  作者：Wei Zou、Zerong Wang、Edith Lacroix、Shih-Hsiung Wu、Harold J Jennings

  DOI：10.1016/s0008-6215(01)00187-2

  日期：2001.8

  Base treatment of O-benzyl protected C-2- or C-4-ulopyranosyl compounds (4 alpha, 4 beta, and 11) by either 10% Et3N or 1% K2CO3 in MeOH initiated a beta elimination to afford alpha,beta-unsaturated C-ulopyranosyl compounds (5 alpha, 5 beta, and 12), which further rearranged in a stereocontrolled manner to multifuctionalized alpha,beta-cyclopentenones (6 and 14) in 70-80% yield. Both C-alpha- and C-beta-2-ulosides (5 alpha and 5 beta) produced the same cyclopentenone 6, indicating that a 1,2-enolate is formed prior to the cleavage of the C-5-O bond. Because 6 is racemic, it was probably formed by the intramolecular cycloaldolization of two equally populated enantiomeric intermediates. When treated with 90% Et3N in MeOH, 5 alpha yielded almost exclusively 15 (isomer of 6), which was formed by a migration of the double bond in 5 alpha during the previously described rearrangement. Thus either 6 or 15 was the major product, depending on the base used. (C) 2001 Elsevier Science Ltd. All rights reserved.