(2S,3R,4S,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol | 108818-01-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol
• 英文别名: (2S,3R,4R,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol；[(2S,3R)-3-[(4R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]oxiran-2-yl]methanol
• CAS: 108818-01-5
• 化学式: C₁₅H₃₀O₅Si
• 分子量: 318.486
• InChiKey: DZNXBBQOXFQFJM-WUHRBBMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol 在 palladium on activated charcoal sodium azide 、 草酰氯 、 二氧化硫 、 四丁基氟化铵 、 水 、 氢气 、 氯化铵 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙二醇二甲醚 、 氯仿 、 乙二醇甲醚 、 水 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 81.25h， 生成 (+)-nojirimycin
  参考文献：
  名称：

  Total synthesis of (+)-nojirimycin and (+)-1-deoxynojirimycin

  摘要：

  DOI：

  10.1021/jo00391a031
• 作为产物：
  描述：

  6-<(tert-butyldimethylsilyl)oxy>-4(S),5(S)-(isopropylidenedioxy)-2(E)-hexen-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 作用下， 生成 (2S,3R,4S,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol
  参考文献：
  名称：

  （+）-α-曲霉霉素的全合成

  摘要：

  利用烯丙醇3作为非碳水化合物手性结构单元，在13个步骤中完成了（+）-α-homonojirimycin的合成，这是天然氮杂庚糖的第一个例子。

  DOI：

  10.1039/c39900001457

文献信息

• Total syntheses of (+)-castanospermine and (+)-1-epicastanospermine and their 1-O-acyl derivatives from a common chiral building block
  作者：Hiroji Ina、Chihiro Kibayashi

  DOI：10.1021/jo00053a015

  日期：1993.1

  Stereoselective total syntheses of (+)-castanospermine (1) and (+)-1-epicastanospermine (2) and their 1-O-acyl derivatives 3-5 have been achieved via a noncarbohydrate-based approach utilizing allylic alcohol 9 as a common chiral building block. Epoxide 10, prepared from 9, underwent regioand stereoselective ring opening with Et2AlN(CH2Ph)2 to give amino alcohol 11, which was converted to aldehyde 15 in four steps. The aldol reaction of 15 with lithio ethyl acetate was predominantly anti selective and generated alpha-hydroxy ester 16 by a nonchelate Felkin-Anh pathway. Compound 16 was transformed into (+)-1-epicastanospermine (2) and its 1-O-acetyl and 1-O-butyryl derivatives (4 and 5) via the lactam intermediate 21. Alternatively, alpha-hydroxy ester 16 was converted to (+)-castanospermine (1) and its 1-O-acetyl derivative (3); these syntheses were achieved via reaction sequences involving the inversion of the C-3 configuration by the Mitsunobu process and 2-fold tandem cyclizations to form the indolizidine skeleton. The results of preliminary biological testing of compounds 2-5 for anti-HIV-1 activity in whole cells are presented.
• Total syntheses of galactosidase inhibitors (+)-galactostatin and (+)-1-deoxygalactostatin
  作者：Sakae Aoyagi、Satoshi Fujimaki、Naoki Yamazaki、Chihiro Kibayashi

  DOI：10.1021/jo00002a057

  日期：1991.1

  beta-Galactosidase inhibitors, (+)-galactostatin and its 1-deoxy analogue (+)-deoxygalactostatin, have been synthesized by utilizing the allylic alcohol 7 as a common chiral building block.
• Aoyagi, Sakae; Fujimaki, Satoshi; Yamazaki, Naoki, Heterocycles, 1990, vol. 30, # 2, p. 783 - 787
  作者：Aoyagi, Sakae、Fujimaki, Satoshi、Yamazaki, Naoki、Kibayashi, Chihiro

  DOI：——

  日期：——
• A total synthesis of (+)-Castanospermine
  作者：Hiroji Ina、Chihiro Kibayashi

  DOI：10.1016/s0040-4039(00)79888-1

  日期：1991.8

  A stereoselective total synthesis of (+)-castanospermine has been achieved via a non-carbohydrate approach utilizing a chiral allylic alcohol as a versatile building block.
• AOYAGI, SAKAE;FUJIMAKI, SATOSHI;KIBAYASHI, CHIHIRO, J. CHEM. SOC. CHEM. COMMUN.,(1990) N0, C. 1457-1459
  作者：AOYAGI, SAKAE、FUJIMAKI, SATOSHI、KIBAYASHI, CHIHIRO

  DOI：——

  日期：——