(2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester | 391658-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,3R,4R,5S,6S,7R)-4,5,6-tris(phenylmethoxy)-7-(phenylmethoxymethyl)-1,8-dioxaspiro[2.5]octane-2-carboxylate
• CAS: 391658-39-2
• 化学式: C₄₀H₄₄O₈
• 分子量: 652.785
• InChiKey: ASOQLTHQVYQIFX-WLRLRXGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 Hydroxy-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester
  参考文献：
  名称：

  Chain Extension of Sugar δ-Lactones with the Enolate of tert-Butyl Bromoacetate and Elaboration into Functionalized C-Ketosides, C-Glycosides, and C-Glucosyl Glycines

  摘要：

  [GRAPHICS]We describe the synthesis of a series of exocyclic sugar epoxides 1 prepared in a one-step procedure from sugar delta -lactones with the enolate of tert-butyl bromoacetate. Ring opening of the sugar oxiranes provides C-ketosides while reduction affords functionalized C-glycosides bearing an a-hydroxy ester moiety. The a-hydroxy ester can be converted into C-glucosyl glycine analogues 2.

  DOI：

  10.1021/ol0102343
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 2,3,4,6-四-O-(苯基甲基)-D-半乳糖酸 D-内酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以61%的产率得到(2S,3S,5R,6S,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Chain Extension of Sugar δ-Lactones with the Enolate of tert-Butyl Bromoacetate and Elaboration into Functionalized C-Ketosides, C-Glycosides, and C-Glucosyl Glycines

  摘要：

  [GRAPHICS]We describe the synthesis of a series of exocyclic sugar epoxides 1 prepared in a one-step procedure from sugar delta -lactones with the enolate of tert-butyl bromoacetate. Ring opening of the sugar oxiranes provides C-ketosides while reduction affords functionalized C-glycosides bearing an a-hydroxy ester moiety. The a-hydroxy ester can be converted into C-glucosyl glycine analogues 2.

  DOI：

  10.1021/ol0102343

文献信息

• Chain Extension of Sugar δ-Lactones with the Enolate of <i>tert-</i>Butyl Bromoacetate and Elaboration into Functionalized <i>C</i>-Ketosides, <i>C</i>-Glycosides, and <i>C</i>-Glucosyl Glycines
  作者：Frank Schweizer、Toshiyuki Inazu

  DOI：10.1021/ol0102343

  日期：2001.12.1

  [GRAPHICS]We describe the synthesis of a series of exocyclic sugar epoxides 1 prepared in a one-step procedure from sugar delta -lactones with the enolate of tert-butyl bromoacetate. Ring opening of the sugar oxiranes provides C-ketosides while reduction affords functionalized C-glycosides bearing an a-hydroxy ester moiety. The a-hydroxy ester can be converted into C-glucosyl glycine analogues 2.