(3R,4S,5S,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester | 173933-53-4

• 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: (3R,4S,5S,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester
• 英文别名: benzyl (3R,4S,5S,6R)-6-(dimethoxymethyl)-4,5-dihydroxy-3-methyloxazinane-2-carboxylate
• CAS: 173933-53-4
• 化学式: C₁₆H₂₃NO₇
• 分子量: 341.361
• InChiKey: XDNSBHXOCOLBME-VZZFWQQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester 在 palladium on activated charcoal sodium hydroxide 、 sodium tetrahydroborate 、 Amberlyst-15 (H⁺) 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 60.0h， 生成 2,5-(benzyloxycarbonylimino)-2,5,6-trideoxy-D-talitol
  参考文献：
  名称：

  Chiral 5-Methyl-trihydroxypyrrolidines—Preparation from 1,2-Oxazines and Glycosidase Inhibitory Properties

  摘要：

  Chemical transformations of chiral 1,2-oxazines 4, 5 gave the 2,5,6-trideoxy-2,5-imino D-alditols 12b, 13b in the D-altritol and D-talitol series, respectively. Basic aldehyde epimerisation led to the D-allitol isomer 15b. Compound 12b is a potent alpha-L-fucosidase and alpha-D-galactosidase inhibitor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01078-9
• 作为产物：
  描述：

  (3R,4R,5S,6R)-6-Dimethoxymethyl-3-methyl-4,5-bis-trifluoromethanesulfonyloxy-[1,2]oxazinane-2-carboxylic acid benzyl ester 在 苯酸四丁基铵 、 sodium carbonate 作用下， 生成 (3R,4S,5S,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  6-Deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and d-series, d-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions

  摘要：

  Nucleophilic ring opening of the cyclic sulfates (+/-)-9c and D-9c and of the epoxide (+/-)-13, or double substitution of the bis-triflate D-10 (derived from the Diels-Alder adduct of hexadienal dimethylacetal to achiral or enantiomerically pure nitroso-derivatives) led to 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, to D-fuco-nojirimycin and to their 1-deoxyderivatives via their crystalline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). 6-Deoxy-nojirimycin and its isomers are mixtures of alpha- and beta-anomers and of the corresponding imine. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00898-3

文献信息

• 6-Deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and d-series, d-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions
  作者：Albert Defoin、Hervé Sarazin、Jacques Streith

  DOI：10.1016/s0040-4020(97)00898-3

  日期：1997.10

  Nucleophilic ring opening of the cyclic sulfates (+/-)-9c and D-9c and of the epoxide (+/-)-13, or double substitution of the bis-triflate D-10 (derived from the Diels-Alder adduct of hexadienal dimethylacetal to achiral or enantiomerically pure nitroso-derivatives) led to 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, to D-fuco-nojirimycin and to their 1-deoxyderivatives via their crystalline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). 6-Deoxy-nojirimycin and its isomers are mixtures of alpha- and beta-anomers and of the corresponding imine. (C) 1997 Elsevier Science Ltd.
• Chiral 5-Methyl-trihydroxypyrrolidines—Preparation from 1,2-Oxazines and Glycosidase Inhibitory Properties
  作者：Thierry Sifferlen、Albert Defoin、Jacques Streith、Didier Le Nouën、Céline Tarnus、Isabelle Dosbaâ、Marie-José Foglietti

  DOI：10.1016/s0040-4020(99)01078-9

  日期：2000.2

  Chemical transformations of chiral 1,2-oxazines 4, 5 gave the 2,5,6-trideoxy-2,5-imino D-alditols 12b, 13b in the D-altritol and D-talitol series, respectively. Basic aldehyde epimerisation led to the D-allitol isomer 15b. Compound 12b is a potent alpha-L-fucosidase and alpha-D-galactosidase inhibitor. (C) 2000 Elsevier Science Ltd. All rights reserved.