1,2,3-tri-O-acetyl-4,6-O-ethylidene-α-D-glucopyranose | 29810-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1,2,3-tri-O-acetyl-4,6-O-ethylidene-α-D-glucopyranose
• 英文别名: [(4aR,6R,7R,8S,8aR)-6,7-diacetyloxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate
• CAS: 29810-01-3
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: FRXAYUBXOIXSRC-IZVWSYFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-acetyl-4,6-O-ethylidene-α-D-glucopyranose 生成 2,3-Di-O-acetyl-4,6-O-ethylidene-D-glucopyranose
  参考文献：
  名称：

  HERZIG, JACOB;NUDELMAN, ABRAHAM;GOTTLIEB, HUGO E., CARBOHYDR. RES., 177,(1988) 21-28

  摘要：

  DOI：
• 作为产物：
  描述：

  4,6-O-乙叉-D-吡喃葡萄糖 、 乙酸酐 反应 95.0h， 生成 1,2,3-tri-O-acetyl-4,6-O-ethylidene-α-D-glucopyranose
  参考文献：
  名称：

  Rapid Preparation of Variously Protected Glycals Using Titanium(III)

  摘要：

  Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)(2). This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. P-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.

  DOI：

  10.1021/jo982447k

文献信息

• The synthesis of two repeating units of haemophilus influenzae type a capsular antigen
  作者：Barbara Grzeszczyk、Anna Banaszek、Aleksander Zamojski

  DOI：10.1016/0008-6215(88)84144-2

  日期：1988.5

  The repeating units 2-O-beta-D-glucopyranosyl-L-ribitol 4'- and 1-phosphate of Haemophilus influenzae type a capsular antigen have been synthesised by condensation of an alpha-D-glucopyranosyl bromide derivative with 5-O-allyl-1,2,3-tri-O-benzyl-D-ribitol followed by selective deprotection of HO-4' or HO-1, phosphorylation, and removal of the blocking groups.

  流感嗜血杆菌型荚膜抗原的重复单元2-O-β-D-吡喃葡萄糖基-L-核糖醇4'-和1-磷酸酯是通过α-D-吡喃葡萄糖基溴化物衍生物与5-O-烯丙基缩合而合成的-1,2,3-三-O-苄基-D-核糖醇，然后对HO-4'或HO-1进行选择性脱保护，磷酸化并去除保护基。
• HERZIG, JACOB;NUDELMAN, ABRAHAM;GOTTLIEB, HUGO E., CARBOHYDR. RES., 177,(1988) 21-28
  作者：HERZIG, JACOB、NUDELMAN, ABRAHAM、GOTTLIEB, HUGO E.

  DOI：——

  日期：——
• GRZESZCZYK, B.;BANASZEK, A.;ZAMOJSKI, A., CARBOHYDR. RES., 175,(1988) N 2, 215-226
  作者：GRZESZCZYK, B.、BANASZEK, A.、ZAMOJSKI, A.

  DOI：——

  日期：——
• Rapid Preparation of Variously Protected Glycals Using Titanium(III)
  作者：Roxanne P. Spencer、Cullen L. Cavallaro、Jeffrey Schwartz

  DOI：10.1021/jo982447k

  日期：1999.5.1

  Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)(2). This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. P-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.