3,4-di-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose | 69908-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4-di-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose
• 英文别名: 3,4-di-O-acetyl-1,2-O-[1-(exo-cyano)-ethylidene]-α-L-rhamnopyranose；3,4-di-O-acetyl-1,2-O-[1-(exo-cyano)ethylidene]-β-L-rhamnopyranose；3,4-di-O-acetyl-1,2-O-(1-cyanoethylidene)-β-L-rhamnopyranose；3,4-di-O-acetyl-1,2-O-exo-cyanoethylidene-β-L-rhamnopyranose；[(2S,3aR,5S,6S,7R,7aR)-7-acetyloxy-2-cyano-2,5-dimethyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6-yl] acetate
• CAS: 69908-87-8
• 化学式: C₁₃H₁₇NO₇
• 分子量: 299.28
• InChiKey: GELNBWRWYKXCAY-DANCAMBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以57%的产率得到4-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose
  参考文献：
  名称：

  Synthesis of Rhamnogalacturonan I Fragments

  摘要：

  The partially deprotected trisaccharide 17 has been synthesized as an analogue of the repeating unit of the backbone of rhamnogalacturonan I. The trisaccharide 17 was obtained after prior selective derivatization of HO-3 and HO-4 of a rhamnopyranose cyanoethylidene glycosyl donor, followed by coupling with a tritylated galactopyranosyluronic acceptor (11), selective removal of the acetyl group at the O-2' position of the formed disaccharide 12, and glycosylation of the HO-2' position with methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-beta-D-galactopyranosid)uronate (14) providing methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-alpha-D-galactopyranosyluronate)-(1-->2)-(4-O-benzoyl-3-O-benzyl-alpha-L-rhamnopyranosyl)-(1-->4)-(allyl 2,3-di-O-benzyl-beta-D-galactopyranosid)uronate (15). Finally, palladium chloride catalyzed deallylation (16) and hydrogenolysis over Pd-C resulted in methyl (methyl alpha-D-galactopyranosyluronate)(1-->2)-(4-O-benzoyl-alpha-L-rhamnopyranosyl)-(1-->4)-alpha/beta D-galactopyranuronate (17).

  DOI：

  10.1080/07328300008544126
• 作为产物：
  描述：

  3,4-di-O-acetyl-1,2-O-<1-(exo-carbamoyl)ethylidene>-β-L-rhamnopyranose 在 吡啶 、 苯甲酰氯 作用下， 反应 16.0h， 以95%的产率得到3,4-di-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose
  参考文献：
  名称：

  Formation of 1,2-0-(1-methoxycarbonyl)ethylidene derivatives of sugars from 1,2-0-(1-cyano)ethylidene derivatives and reverse transformation

  摘要：

  DOI：

  10.1007/bf00956363

文献信息

• Efficient stereocontrolled synthesis of C-glycosides using glycosyl donors substituted by propane 1,3-diyl phosphate as the leaving group
  作者：Gurdial Singh、Hariprasad Vankayalapati

  DOI：10.1016/s0957-4166(01)00305-6

  日期：2001.7

  a- and beta -Glycosyl cyanides, per-O-acetyl-1,2-O-1-cyanoethylidenes and C-allyl glycopyranosides were efficiently prepared by treatment of 2,3,4-tri-O-acetyl-alpha,beta -L-rhamno-, L-fuco- and 2,3,4,6-tetra-O-acetyl-alpha,beta -D-galactopyranosyl propane-1,3-diyl phosphates with trimethylsilyl cyanide (TMSCN) and allyltrimethylsilane in the presence of trimethylsilyl triflate (TMSOTf). Similarly 2,3,4,6-tetra-O-benzyl-alpha,beta -D-manno- and D-glucopyranosyl propane-1,3-diyl phosphates were employed in the synthesis of C-glycosides. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of the O-specific polysaccharide of
  作者：N.K. Kochetkov、N.É. Byramova、Yu.E. Tsvetkov、L.V. Backinowsky

  DOI：10.1016/s0040-4020(01)96688-8

  日期：1985.1
• Selective removal of O-acetyl groups in the presence of O-benzoyl groups by acid-catalysed methanolysis
  作者：Narguiz É. Byramova、Michael V. Ovchinnikov、Leon V. Backinowsky、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(83)88370-0

  日期：1983.12
• Synthesis of the principal chain of the o-antigenic polysaccharides ofShigella flexneri. Communication 3. Synthesis of 4-o-benzoyl-3-o-(2-o-acetyl-3,4-di-o-benzoyl-?-L-rhamnopyranosyl)-1,2-o-[1-(exocyano)� ethyliden]-?-L-rhamnopyranose
  作者：N. �. Bairamova、L. V. Bakinovskii、N. K. Kochetkov

  DOI：10.1007/bf01142797

  日期：1985.5
• Reactivity of 1,2-O-cyanoalkylidene sugar derivatives in trityl-cyanoalkylidene condensation
  作者：P. I. Kitov、Yu. E. Tsvetkov、L. V. Backinowsky、N. K. Kochetkov

  DOI：10.1007/bf00699947

  日期：1993.8

  The rate-determining step of trityl-cyanoalkylidene condensation is the interaction between the cyanoalkylidene derivative (CD) and the triphenylmethyl cation. The rate of the reaction follows first-order kinetics with respect to both CD and the catalyst (Tr+) and is independent of the nature and concentration of the trityl ether. Glycosylation rate constants have been determined for CD's of most common monosaccharides.