benzyl N-[(2S,3S,4S,6S)-4-hydroxy-6-[(1R)-2-hydroxy-1-phenylethoxy]-2-methyloxan-3-yl]carbamate | 201158-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-[(2S,3S,4S,6S)-4-hydroxy-6-[(1R)-2-hydroxy-1-phenylethoxy]-2-methyloxan-3-yl]carbamate
• CAS: 201158-82-9
• 化学式: C₂₂H₂₇NO₆
• 分子量: 401.459
• InChiKey: REKYPBMXPVNWNH-DXUGQKIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S,3S,4S,6S)-4-hydroxy-6-[(1R)-2-hydroxy-1-phenylethoxy]-2-methyloxan-3-yl]carbamate 在 palladium on activated charcoal 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 97.17h， 生成 [(2R)-2-[(2S,4S,5S,6S)-5-(dimethylamino)-4-hydroxy-6-methyloxan-2-yl]oxy-2-phenylethyl] (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoate
  参考文献：
  名称：

  Diastereoselective Synthesis of the Monosaccharide Kedarosamine and Incorporation in an Analogue of the Enediyne Kedarcidin Chromophore

  摘要：

  Kedarcidin chromophore, as with most enediyne antitumor antibiotics, contains unusual monosaccharide moieties. Synthesis of one of these moieties, the 2,4,6-trideoxy-4-dimethylaminohexose kedarosamine, from D-threonine and incorporation into an analogue of kedarcidin chromophore (1) is described herein. Conversion of D-threonine into allyl ketone 7 and stereoselective reduction by using tetramethylammonium triacetoxyborohydride for intramolecular hydride delivery were key steps in the preparation of kedarosamine. A thioglycoside derivative of kedarosamine (12) was found to be less efficient as a glycosyl donor, whereas a 1-O-acetate (15) gave the desired alpha-glycoside exclusively in 60-80% yield when treated with borontrifluoride etherate. Use of a Cbz instead of a Fmoc protecting group for the C-4 amino group of kedarosamine was essential for the successful preparation of analogue 1. Finally, dimethylation of the amino group at C-4 of kedarosamine was found to require careful adjustment of the reaction conditions in order to avoid byproduct formation.

  DOI：

  10.1021/jo971380i
• 作为产物：
  描述：

  N-苄氧羰基-D-苏氨酸 在 吡啶 、 三聚氯氰 、 QF-3H₂O 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 、 臭氧 、 三氟乙酸 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 溶剂黄146 、 乙腈 、 苯 为溶剂， 反应 67.75h， 生成 benzyl N-[(2S,3S,4S,6S)-4-hydroxy-6-[(1R)-2-hydroxy-1-phenylethoxy]-2-methyloxan-3-yl]carbamate
  参考文献：
  名称：

  Diastereoselective Synthesis of the Monosaccharide Kedarosamine and Incorporation in an Analogue of the Enediyne Kedarcidin Chromophore

  摘要：

  Kedarcidin chromophore, as with most enediyne antitumor antibiotics, contains unusual monosaccharide moieties. Synthesis of one of these moieties, the 2,4,6-trideoxy-4-dimethylaminohexose kedarosamine, from D-threonine and incorporation into an analogue of kedarcidin chromophore (1) is described herein. Conversion of D-threonine into allyl ketone 7 and stereoselective reduction by using tetramethylammonium triacetoxyborohydride for intramolecular hydride delivery were key steps in the preparation of kedarosamine. A thioglycoside derivative of kedarosamine (12) was found to be less efficient as a glycosyl donor, whereas a 1-O-acetate (15) gave the desired alpha-glycoside exclusively in 60-80% yield when treated with borontrifluoride etherate. Use of a Cbz instead of a Fmoc protecting group for the C-4 amino group of kedarosamine was essential for the successful preparation of analogue 1. Finally, dimethylation of the amino group at C-4 of kedarosamine was found to require careful adjustment of the reaction conditions in order to avoid byproduct formation.

  DOI：

  10.1021/jo971380i

文献信息

• Diastereoselective Synthesis of the Monosaccharide Kedarosamine and Incorporation in an Analogue of the Enediyne Kedarcidin Chromophore
  作者：Tatjana Vuljanic、Jan Kihlberg、Peter Somfai

  DOI：10.1021/jo971380i

  日期：1998.1.1

  Kedarcidin chromophore, as with most enediyne antitumor antibiotics, contains unusual monosaccharide moieties. Synthesis of one of these moieties, the 2,4,6-trideoxy-4-dimethylaminohexose kedarosamine, from D-threonine and incorporation into an analogue of kedarcidin chromophore (1) is described herein. Conversion of D-threonine into allyl ketone 7 and stereoselective reduction by using tetramethylammonium triacetoxyborohydride for intramolecular hydride delivery were key steps in the preparation of kedarosamine. A thioglycoside derivative of kedarosamine (12) was found to be less efficient as a glycosyl donor, whereas a 1-O-acetate (15) gave the desired alpha-glycoside exclusively in 60-80% yield when treated with borontrifluoride etherate. Use of a Cbz instead of a Fmoc protecting group for the C-4 amino group of kedarosamine was essential for the successful preparation of analogue 1. Finally, dimethylation of the amino group at C-4 of kedarosamine was found to require careful adjustment of the reaction conditions in order to avoid byproduct formation.