(2R,3S)-toluene-4-sulfonic acid 4-benzyloxycarbonylamino-3-hydroxy-5-oxotetrahydrofuran-2-ylmethyl ester | 654083-23-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S)-toluene-4-sulfonic acid 4-benzyloxycarbonylamino-3-hydroxy-5-oxotetrahydrofuran-2-ylmethyl ester
• CAS: 654083-23-5
• 化学式: C₂₀H₂₁NO₈S
• 分子量: 435.455
• InChiKey: PWOZKNIZZDCDCR-GVYDCBATSA-N

反应信息

• 作为反应物：
  描述：

  (2R,3S)-toluene-4-sulfonic acid 4-benzyloxycarbonylamino-3-hydroxy-5-oxotetrahydrofuran-2-ylmethyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 1,4-二氧六环 、 水 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 3.0h， 生成 (2R,3S)-toluene-4-sulfonic acid 4-amino-3-hydroxy-5-oxotetrahydrofuran-2-ylmethyl ester
  参考文献：
  名称：

  Total synthesis of 3,4-dihydroxyprolines, d-threo-l-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester

  摘要：

  The Henry reaction between D-glyceraldehyde and ethyl nitroacetate allowed the practical development of a diastereoselective synthesis of 3,4,5-trihydroxy-2-nitropentanoic acid esters, which were reduced to polyoxamic acids, which were used in a new diastereoselective synthesis of 3,4-dihydroxyprolines and new enantioselective syntheses Of D-threo-L-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.005
• 作为产物：
  描述：

  对甲苯磺酰氯 、 (4S,5R)-(4-hydroxy-5-hydroxymethyl-2-oxotetrahydrofuran-3-yl)carbamic acid benzyl ester 在 吡啶 作用下， 反应 20.0h， 以70%的产率得到(2R,3S)-toluene-4-sulfonic acid 4-benzyloxycarbonylamino-3-hydroxy-5-oxotetrahydrofuran-2-ylmethyl ester
  参考文献：
  名称：

  Total synthesis of 3,4-dihydroxyprolines, d-threo-l-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester

  摘要：

  The Henry reaction between D-glyceraldehyde and ethyl nitroacetate allowed the practical development of a diastereoselective synthesis of 3,4,5-trihydroxy-2-nitropentanoic acid esters, which were reduced to polyoxamic acids, which were used in a new diastereoselective synthesis of 3,4-dihydroxyprolines and new enantioselective syntheses Of D-threo-L-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.005