(R*,R*)-γ-amino-β-(phenylmethoxy)-1,3-dithiolane-2-propanol | 124010-26-0

• 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: (R*,R*)-γ-amino-β-(phenylmethoxy)-1,3-dithiolane-2-propanol
• CAS: 124010-26-0；124010-27-1
• 化学式: C₁₃H₁₉NO₂S₂
• 分子量: 285.431
• InChiKey: MBSYQRXVIUTLCY-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.48
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4,5-dihydro-3-(1,3-dithiolan-2-yl)-4-isoxazole 在 锂硼氢 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 97.58h， 生成 (R*,R*)-γ-amino-β-(phenylmethoxy)-1,3-dithiolane-2-propanol
  参考文献：
  名称：

  2-Amino-2-deoxytetrose Derivatives. Preparation from 4,5-Dihydroisoxazoles via Reductive Cleavage

  摘要：

  The 4-alkoxy-3-nitro-4,5-dihydroisoxazoles 2a,b were prepared by condensation of nitromethane and chloroacetaldehyde, protection of the resulting nitroaldol Ic, and subsequent nitrosative cyclization. Multistep replacement of the nitro group of 2a,b by a 2-(1,3-dithiolanyl) group gave 7a,b. Reaction of 7b with lithium borohydride afforded reductive cleavage of the dihydroisoxazole ring to produce the open-chain diastereomeric amino alcohols 6a,b. A reproducible ratio of > 90: 10 6a/6b was obtained using freshly prepared hydride reagent. The amino alcohols were converted to the corresponding (R*,R*)-amide 6c and (R*,S*)-amide 6d which were chromatographically separated. The(R*,R*)-amide was transformed into the 2-amino-2-deoxythreose derivatives 11a,b and hence to 12 while the (R*,S*)-amide was similarly transformed to 2-amino-2-deoxyerythrose derivative 14a and its anomeric isomer 14b.

  DOI：

  10.1021/jo00125a015

文献信息

• A new route to 4-oxygenated isoxazolines. Application to the synthesis of 2-deoxy-2-aminobutose derivatives
  作者：Peter A. Wade、David T. Price

  DOI：10.1016/s0040-4039(00)72711-0

  日期：1989.1

  The THP ether of 4,5-dihydro-3-nitro-4-isoxazolol, prepared by a sequential nitroaldol nitrosative cyclization strategy, was converted to a 4,5-dihydro-3-(dithiolanyl)isoxazole; subsequent LBH reduction gave a 95:5 diastereomeric mixture of 2-deoxy-2-aminothreose and -erythrose derivatives, respectively, which was cyclized to a mixture of tetrahydro-2H-1,3-oxazine-2-ones.

  通过连续的硝基缩醛亚硝化环化策略制备的4，5-二氢-3-硝基-4-异恶唑的THP醚被转化为4，5-二氢-3-（二硫代戊酰基）异恶唑。随后的LBH还原分别得到2-脱氧-2-氨基苏糖和-赤藓糖衍生物的95：5非对映异构体混合物，将其环化为四氢-2 H -1,3-恶嗪-2-酮的混合物。