5,6-O-isopropylidene-1,2-O-trichloroethylidene-α-D-glucofuranose | 88390-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-O-isopropylidene-1,2-O-trichloroethylidene-α-D-glucofuranose
• 英文别名: 5,6-O-isopropylidene-1,2-O-(S)-trichloroethylidene-α-D-glucofuranose；(2S,3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(trichloromethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 88390-56-1
• 化学式: C₁₁H₁₅Cl₃O₆
• 分子量: 349.596
• InChiKey: HXMVIMDRNMGVDY-IQBJDPKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-O-isopropylidene-1,2-O-trichloroethylidene-α-D-glucofuranose 在 盐酸 、 sodium periodate 、 水 、 barium(II) oxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 5-(E)-eno-3-O-methyl-1,2-O-(S)-trichloroethylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose
  参考文献：
  名称：

  Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-d-xylo-oct-1,4-furano-7-uloses

  摘要：

  Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-tride-oxy-alpha-D-xylo-oct-1,4-furano-7-uloses (1 a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo alkyl, on the 1,2-O-alkylidene group and its size, resulted in an increase of the yield of the 4S isomers. 3-O-Acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3-O-methyl derivatives gave pure single stereoisomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.09.006
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 β-氯醛糖 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到5,6-O-isopropylidene-1,2-O-trichloroethylidene-α-D-glucofuranose
  参考文献：
  名称：

  Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-d-xylo-oct-1,4-furano-7-uloses

  摘要：

  Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-tride-oxy-alpha-D-xylo-oct-1,4-furano-7-uloses (1 a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo alkyl, on the 1,2-O-alkylidene group and its size, resulted in an increase of the yield of the 4S isomers. 3-O-Acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3-O-methyl derivatives gave pure single stereoisomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.09.006

文献信息

• Syntheses and Characterization of New 3-O-Allyl Ether Chloralose Derivatives
  作者：Fatma Çetin Telli

  DOI：10.14233/ajchem.2015.17975

  日期：——

  The new 3-O-allyl ether derivatives of sugar were synthesized with high yield and mild reaction conditions. The synthesis of 3-O-acetylchloralose derivatives (5-8) and 3-O-allyl ether chloralose derivatives (9-12) were carried out. These new 3-O-allyl ether of chloralose derivatives are potential monomers for the synthesis of new glycopolymers.

  新型3-O-烯丙基醚糖衍生物在高产率和温和反应条件下合成成功。合成了3-O-乙酰氯醇糖衍生物（5-8）和3-O-烯丙基醚氯醇糖衍生物（9-12）。这些新型3-O-烯丙基醚氯醇糖衍生物是合成新型糖聚合物的潜在单体。
• Effects of the trichloromethyl group in displacement reactions of some 3-O-tosyl-1,2-O-trichloroethylidene-α-d-galacto- and -gluco-furanose derivatives
  作者：Hüseyin Anil、Levent Yüceer

  DOI：10.1016/0008-6215(83)88486-9

  日期：1983.11
• Selective Wittig olefination in aqueous media for the rapid preparation of unsaturated 7,3-lactone-α-d-xylofuranose derivatives
  作者：Elsie Ramirez、Mario Sánchez、Rosa L. Meza-León、Leticia Quintero、Fernando Sartillo-Piscil

  DOI：10.1016/j.tetlet.2010.02.094

  日期：2010.4

  A highly efficient and rapid protocol for the preparation of the title compounds 1a and 1b from D-glucose derivatives 2a and 2b, respectively, is reported. To this end, highly selective Wittig olefination in aqueous media was developed for the elaboration of alpha,beta-unsaturated acids 5a and 5b, which when treated with DCC, lactonization was accomplished and the title compounds 1a and 1b were obtained in only three sequential steps with overall yields of 85% and 88%, respectively. Additionally, the Z-selectivity was studied by analyzing conformational models of its corresponding oxophosphorinane intermediaries. (c) 2010 Elsevier Ltd. All rights reserved.
• Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-d-xylo-oct-1,4-furano-7-uloses
  作者：Fatma Çetin、Nilgün Yenil、Levent Yüceer

  DOI：10.1016/j.carres.2005.09.006

  日期：2005.12

  Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-tride-oxy-alpha-D-xylo-oct-1,4-furano-7-uloses (1 a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo alkyl, on the 1,2-O-alkylidene group and its size, resulted in an increase of the yield of the 4S isomers. 3-O-Acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3-O-methyl derivatives gave pure single stereoisomers. (c) 2005 Elsevier Ltd. All rights reserved.