1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside | 53269-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
• 英文别名: 1',2,3,3',4,6,6'-hepta-O-acetylsucrose；2,3,4,6,1',3',6'-Hepta-O-acetylsucrose；2,3,4,6,1',3',6'-heptaacetyl sucrose；1',2,3,3',4,6,6'-Heptaacetyl-sucrose；[(2R,3R,4S,5S)-4-acetyloxy-5-(acetyloxymethyl)-3-hydroxy-5-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl acetate
• CAS: 53269-83-3
• 化学式: C₂₆H₃₆O₁₈
• 分子量: 636.561
• InChiKey: NXCQIOXFNWBNKB-PNQDPTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  232
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 、 乙酸酐-d6 在 氘代吡啶 作用下， 生成 perdeuteroacetylated 2,3,4,6,1',3',6'-heptaacetyl sucrose
  参考文献：
  名称：

  蔗糖八乙酸酯在有机溶剂中的区域选择性酶促脱乙酰作用

  摘要：

  报道了在有机溶剂中使用蛋白酶和脂肪酶使蔗糖八乙酸酯脱乙酰化的第一个实例。产物蔗糖的七乙酸，六乙酸和五乙酸酯的区域化学是通过全氘代乙酰化和1 H-NMR确定的。实现了高强度甜味剂三氯蔗糖的商业合成中关键中间体的制备。

  DOI：

  10.1016/0040-4039(94)88316-5
• 作为产物：
  描述：

  蔗糖八乙酸酯 在 lipase type II from porcine pancreas 作用下， 以 异丙醚 为溶剂， 反应 24.0h， 生成 1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  蔗糖八乙酸酯在有机溶剂中的区域选择性酶促脱乙酰作用

  摘要：

  报道了在有机溶剂中使用蛋白酶和脂肪酶使蔗糖八乙酸酯脱乙酰化的第一个实例。产物蔗糖的七乙酸，六乙酸和五乙酸酯的区域化学是通过全氘代乙酰化和1 H-NMR确定的。实现了高强度甜味剂三氯蔗糖的商业合成中关键中间体的制备。

  DOI：

  10.1016/0040-4039(94)88316-5

文献信息

• Regioselective enzymic deacetylation of octa-O-acetyl-sucrose: preparation of hepta-O-acetylsucroses
  作者：Kung-Yao Chang、Shih-Hsiung Wu、Kung-Tsung Wang

  DOI：10.1016/0008-6215(91)89011-4

  日期：1991.12

  Deacetylation of octa-O-acetylsucrose (1) with Alcalase or protease N gave the 2,3,4,6,3',4',6'-hepta-acetate (2) as the initial major product with the 2,3,4,6,3',4'-hexa-acetate (3) as the subsequent main product. The 2,3,4,1',3',4',6'-hepta-acetate (5) was obtained from 1 by the action of lipase OF or lipase AP6, and the 2,3,4,6,1',3',6'-(4) and 2,3,4,6,1',3',4'-hepta-acetate (7) by the action of

  用Alcalase或蛋白酶N使八-O-乙酰基蔗糖（1）脱乙酰化，得到2,3,4,6,3'，4'，6'-庚酸酯（2）为初始主要产物，其中2,3 ，4,6,3'，4'-六乙酸酯（3）作为后续的主要产物。2,1,2,3,4,1'，3'，4'，6'-庚酸酯（5）是通过脂肪酶OF或脂肪酶AP6的作用从1，以及2,3,4,6,1 '，3'，6'-（4）和2,3,4,6,1'，3'，4'-七乙酸酯（7）分别通过念珠菌脂肪酶和胰凝乳蛋白酶作用。2,5,6,1'，3'，4'，6'-庚酸酯（6）由5通过酰基转移形成。
• Regio-selective deprotection of peracetylated sugars via lipase hydrolysis
  作者：Gloria Fernandez-Lorente、Jose M Palomo、Jany Cocca、Cesar Mateo、Paola Moro、Marco Terreni、Roberto Fernandez-Lafuente、Jose M Guisan

  DOI：10.1016/s0040-4020(03)00876-7

  日期：2003.7

  Purified lipases (via inter-facial activation on hydrophobic supports) from different microbial extracts have been evaluated in the regio-selective hydrolysis of peracetylated sugars (peracetylated glucose, ribose and sucrose). Among the enzymes tested, lipases from Candida rugosa (CRL) and from Pseudomonas fluorescens (PFL) exhibited the best properties in these reactions. Then, we have prepared two different immobilized lipase preparations obtained by interfacial activation on hydrophobic supports or by covalent attachment on glutaraldehyde agarose. Interfacially activated lipases exhibited a higher activity than covalently attached enzymes (even by a 100-fold factor), giving the higher yields of mono deacetylated sugars (in some instances by more than a threefold factor) in short reaction times. In the hydrolysis of 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose catalyzed by PFL adsorbed on octyl agarosa, hydrolyzed mainly the 3 position (30% of yield) while the CRL gave the hydrolysis only in position 5 (about 50% of yield). Depending on the enzyme immobilized preparation, we have been able also to obtain selective hydrolysis of 1,2,3,4,6-penta-O-acetyl-alpha/beta-D-glucopyranose obtaining a free hydroxyl group in position 1, 4 or 6. Moreover, selective hydrolysis in the 4' position of peracetylated sucrose was achieved when the hydrolysis is performed with CRL immobilized on octyl-agarose (yield was 77%). (C) 2003 Elsevier Ltd. All rights reserved.
• Capek, Karel; Vodrazkova-Medonosova, Monika; Moravcova, Jitka, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 7, p. 1476 - 1486
  作者：Capek, Karel、Vodrazkova-Medonosova, Monika、Moravcova, Jitka、Sedmera, Petr

  DOI：——

  日期：——
• Capek, Karel; Vydra, Tomas; Sedmera, Petr, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 6, p. 1317 - 1332
  作者：Capek, Karel、Vydra, Tomas、Sedmera, Petr

  DOI：——

  日期：——
• Franzkowiak, Monika; Thiem, Joachim, Liebigs Annalen der Chemie, 1987, p. 1065 - 1072
  作者：Franzkowiak, Monika、Thiem, Joachim

  DOI：——

  日期：——