5-O-Benzyl-3-desoxy-3-dimethylamino-2-O-methanesulfonyl-α-D-arabinofuranoside de methyle | 143604-46-0

• 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: 5-O-Benzyl-3-desoxy-3-dimethylamino-2-O-methanesulfonyl-α-D-arabinofuranoside de methyle
• 英文别名: [(2S,3S,4R,5S)-4-(dimethylamino)-2-methoxy-5-(phenylmethoxymethyl)oxolan-3-yl] methanesulfonate
• CAS: 143604-46-0
• 化学式: C₁₆H₂₅NO₆S
• 分子量: 359.444
• InChiKey: FJLQJPGQMYQCPA-WCVJEAGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-O-Benzyl-3-desoxy-3-dimethylamino-2-O-methanesulfonyl-α-D-arabinofuranoside de methyle 在 sodium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-O-Benzyl-2-desoxy-2-dimethylamino-3-O-methanesulfonyl-α-D-xylofuranoside de methyle
  参考文献：
  名称：

  Synthese et equilibre thermodynamique des huit 5-O-benzyl-2- (ou 3)- dimethylamino-3 (ou 2)-O-mesyl-α (ou β)-D- (ou ) - furanosides de methyle

  摘要：

  Regioselectivity of the opening of 2,3-anhydrofuranosides 1 (alpha and beta) and 2 (alpha and beta) by dimethylamine (and by ammonia for 1) has been determined. Thermic stability of the eight corresponding vic-dimethylaminomesylates 11-14 (alpha and beta) in CD3CN and C6D6 has been studied by H-1 NMR : in each case steric hindrance seems to be the determinant factor of the four thermodynamic equilibria 11 reversible 12 (alpha and beta) and 13 reversible 14 (alpha and beta); aziridinium ions are assumed to be formed as intermediates and one of them has been effectively observed.

  DOI：

  10.1016/s0040-4020(01)90122-x
• 作为产物：
  描述：

  Methyl 2,3-anhydro-5-O-benzyl-α-D-lyxofuranoside 在 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 5-O-Benzyl-3-desoxy-3-dimethylamino-2-O-methanesulfonyl-α-D-arabinofuranoside de methyle
  参考文献：
  名称：

  Synthese et equilibre thermodynamique des huit 5-O-benzyl-2- (ou 3)- dimethylamino-3 (ou 2)-O-mesyl-α (ou β)-D- (ou ) - furanosides de methyle

  摘要：

  Regioselectivity of the opening of 2,3-anhydrofuranosides 1 (alpha and beta) and 2 (alpha and beta) by dimethylamine (and by ammonia for 1) has been determined. Thermic stability of the eight corresponding vic-dimethylaminomesylates 11-14 (alpha and beta) in CD3CN and C6D6 has been studied by H-1 NMR : in each case steric hindrance seems to be the determinant factor of the four thermodynamic equilibria 11 reversible 12 (alpha and beta) and 13 reversible 14 (alpha and beta); aziridinium ions are assumed to be formed as intermediates and one of them has been effectively observed.

  DOI：

  10.1016/s0040-4020(01)90122-x

文献信息

• Fluorination by anchimeric assistance of a diallylamino group: application to the synthesis of some methyl aminofluoropentofuranosides
  作者：Marie-Béatrice Giudicelli、Marie-Agnès Thomé、Dominique Picq、Daniel Anker

  DOI：10.1016/0008-6215(93)84057-d

  日期：1993.10

  Methyl 2,3-trans-dialkylaminofluoro-alpha(or beta)-D-pentofuranosides were prepared by fluorination wherein the dialkylamino, group assists the replacement of a trans-vicinal mesylate. Whatever the location of the dialkylamino group (alpha or beta face of the ring), the regioselectivity of fluorination depends mainly on the alpha or beta orientation of the anomeric methoxyl group. The use of a diallylamino substituent led to methyl 3-amino-2,3-dideoxy-2-fluoro-beta-D-xylofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-alpha-D-arabinofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-beta-D-xylofuranoside, and methyl 3-amino-2,3-dideoxy-2-fluoro-alpha-D-arabinofuranoside. Attempts to obtain 2(or 3),5-difluoro analogues staring from corresponding dimesylates gave only disappointing results.
• Synthese et equilibre thermodynamique des huit 5-O-benzyl-2- (ou 3)- dimethylamino-3 (ou 2)-O-mesyl-α (ou β)-D- (ou ) - furanosides de methyle
  作者：Marie-Béatrice Giudicelli、Marie-Agnès Thomé、Dominique Picq、Daniel Anker

  DOI：10.1016/s0040-4020(01)90122-x

  日期：1992.1

  Regioselectivity of the opening of 2,3-anhydrofuranosides 1 (alpha and beta) and 2 (alpha and beta) by dimethylamine (and by ammonia for 1) has been determined. Thermic stability of the eight corresponding vic-dimethylaminomesylates 11-14 (alpha and beta) in CD3CN and C6D6 has been studied by H-1 NMR : in each case steric hindrance seems to be the determinant factor of the four thermodynamic equilibria 11 reversible 12 (alpha and beta) and 13 reversible 14 (alpha and beta); aziridinium ions are assumed to be formed as intermediates and one of them has been effectively observed.