isopropyl 7-[[(1'S)-1'-phenylethyl]amino]-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galactooctopyranuronate | 206127-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 7-[[(1'S)-1'-phenylethyl]amino]-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galactooctopyranuronate
• 英文别名: propan-2-yl (2S)-2-[[(1S)-1-phenylethyl]amino]-3-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]propanoate
• CAS: 206127-70-0
• 化学式: C₂₅H₃₇NO₇
• 分子量: 463.571
• InChiKey: FWMGQXFROIHSSD-GXSNOCKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isopropyl 7-[[(1'S)-1'-phenylethyl]amino]-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galactooctopyranuronate 在 氢氧化钾 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 8.5h， 生成 isopropyl 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[(1'S)-1'-phenylethyl]amino]-L-glycero-α-D-galactooctopyranuronoyl]amino]-L-glycero-α-D-galactooctopyranuronate
  参考文献：
  名称：

  Synthesis of new glycosyl-α-aminoacid derivatives for glycopeptide chemistry

  摘要：

  The synthesis of new N- or C-protected glycosyl-alpha -aminoacids and their use to prepare new glycopeptides is described. The overall synthetic strategy to obtain these new alpha -aminoacid chirons involves four distinct steps from dialdoses: (1) a diastereoselective Darzens reaction between the potassium anion derived from isopropyl dichloroacetate and a suitable protected dialdose, (2) the one-pot transformation of the so-obtained isopropyl glycosyl-alpha -chloroglycidic ester with magnesium iodide, then sodium hydrogenosulfite, into an isopropyl glycosyl-alpha -ketoester, (3) the reductive amination of the alpha -ketoester with (S)-alpha -methylbenzylamine and an hydrogenating reagent, (4) N- or C-selective deprotection and further peptidic coupling. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00600-7
• 作为产物：
  描述：

  二氯乙酸异丙酯 在 palladium on activated charcoal molecular sieve 、 水 、 氢气 、 potassium isopropoxide 、 sodium hydrogensulfite 、 magnesium iodide 作用下， 以 乙醚 、 异丙醇 为溶剂， 35.0 ℃ 、1000.0 kPa 条件下， 反应 32.0h， 生成 isopropyl 7-[[(1'S)-1'-phenylethyl]amino]-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galactooctopyranuronate
  参考文献：
  名称：

  用于糖肽化学的新型多功能糖基α-氨基酸衍生物

  摘要：

  在 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose 1 的 C-6 处用 α-酮酯单元进行扩链，然后催化还原胺化α-酮基导致新的受保护的 2-(1',2':3',4'-di-O-isopropylidene-6'-deoxy-α-D-galactopyranosyl) 甘氨酸非对映异构体 6 和 6'，它们很容易分开。α-氨基酸部分的 N 或 C 保护基团的化学选择性去除允许随后将这些 6-脱氧-α-D-吡喃半乳糖基甘氨酸残基插入肽链中。

  DOI：

  10.1055/s-1998-1660

文献信息

• New glycosyl α-hydroxyesters as key intermediates in a convenient route to glycosyl α-aminoester chirons
  作者：Claude Grison、Frédéric Coutrot、Philippe Coutrot

  DOI：10.1016/s0040-4020(02)00193-x

  日期：2002.4

  examines the stereoselective preparation of glycosyl α-hydroxyesters via the asymmetric reduction of glycosyl α-ketoesters, using various chiral or achiral reagents and Bakers' yeast. The diastereomeric excess could exceed 98% for the galacto-series. These glycosyl α-hydroxyesters are used as chiral precursors for the diastereoselective synthesis of glycosyl α-aminoesters synthons.

  本文研究了使用各种手性或非手性试剂和贝克酵母，通过不对称还原糖基α-酮酸酯的立体选择性制备方法。半乳糖系列的非对映异构体过量可能超过98％。这些糖基α-羟基酯被用作手性前体，用于糖基α-氨基酯合成子的非对映选择性合成。
• A Novel Versatile Glycosyl <i>α</i>-Aminoacid Derivative for Glycopeptidic Chemistry
  作者：Philippe Coutrot、Claude Grison、Frédéric Coutrot

  DOI：10.1055/s-1998-1660

  日期：1998.4

  The chain extension with an α-ketoester unit at C-6 of 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose 1 followed by a catalytic reductive amination of the α-keto group led to the novel protected 2-(1′,2′:3′,4′-di-O-isopropylidene-6′-deoxy-α-D-galactopyranosyl) glycine diastereomers 6 and 6′ which are easy to separate. Chemoselective removal of N- or C-protecting groups at the α-aminoacid

  在 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose 1 的 C-6 处用 α-酮酯单元进行扩链，然后催化还原胺化α-酮基导致新的受保护的 2-(1',2':3',4'-di-O-isopropylidene-6'-deoxy-α-D-galactopyranosyl) 甘氨酸非对映异构体 6 和 6'，它们很容易分开。α-氨基酸部分的 N 或 C 保护基团的化学选择性去除允许随后将这些 6-脱氧-α-D-吡喃半乳糖基甘氨酸残基插入肽链中。
• Synthesis of new glycosyl-α-aminoacid derivatives for glycopeptide chemistry
  作者：Claude Grison、Frédéric Coutrot、Philippe Coutrot

  DOI：10.1016/s0040-4020(01)00600-7

  日期：2001.7

  The synthesis of new N- or C-protected glycosyl-alpha -aminoacids and their use to prepare new glycopeptides is described. The overall synthetic strategy to obtain these new alpha -aminoacid chirons involves four distinct steps from dialdoses: (1) a diastereoselective Darzens reaction between the potassium anion derived from isopropyl dichloroacetate and a suitable protected dialdose, (2) the one-pot transformation of the so-obtained isopropyl glycosyl-alpha -chloroglycidic ester with magnesium iodide, then sodium hydrogenosulfite, into an isopropyl glycosyl-alpha -ketoester, (3) the reductive amination of the alpha -ketoester with (S)-alpha -methylbenzylamine and an hydrogenating reagent, (4) N- or C-selective deprotection and further peptidic coupling. (C) 2001 Elsevier Science Ltd. All rights reserved.