methyl 4-O-benzoyl-2,3-O-isopropylidene-α-D-rhamnopyranoside | 85726-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzoyl-2,3-O-isopropylidene-α-D-rhamnopyranoside
• 英文别名: [(3aS,4S,6R,7R,7aS)-4-methoxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] benzoate
• CAS: 85726-76-7
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: RTLLRDPZZTULOI-TZHJVIJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzoyl-2,3-O-isopropylidene-α-D-rhamnopyranoside 在 盐酸 、 重铬酸吡啶 、 三正丁基氢锡 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 zinc dibromide 作用下， 以 甲醇 、 硝基甲烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 Benzyl-O-(4-O-benzoyl-2,6-didesoxy-β-D-erythro-hexopyranosid-3-ulose)-(1->3)-O-(4-O-benzoyl-2,6-didesoxy-β-D-arabino-hexopyranosyl)-(1->3)-4-O-benzoyl-2,6-didesoxy-β-D-arabino-hexopyranosid
  参考文献：
  名称：

  利用二溴甲基甲基醚反应形成金葡糖酸低聚脱氧单糖，二糖和三糖

  摘要：

  用二溴甲基甲基醚处理从甘露糖得到的2，3-异亚丙基D-鼠李吡喃糖苷2，得到2，6-二脱氧-2-溴-吡喃葡糖基溴化物5。相应地，D-talo前体3产生了异构半乳糖。 -吡喃基溴化物4.通过三氟甲磺酸银催化选择性地将两种吡喃葡萄糖基溴化物糖基化，以仅得到β，1-3连接的吡喃葡萄糖基化物。用mCPBA将3-exo-亚甲基组分环氧化，在还原性环氧乙烷打开后，得到3-C-甲基-β-D-核糖-己吡喃糖苷结构17。相应的堆积导致三糖结构21。亚甲基衍生物25，其环氧化成26和还原性开放，立体选择性地产生了全β-连接的甲基支链三糖27，代表了光神霉素EDC-三糖。

  DOI：

  10.1080/07328303.2017.1397682
• 作为产物：
  描述：

  Methyl 4,6-O-benzylidene-2,3-O-isopropylidene-α-D-mannopyranoside 在 nickel dichloride N-溴代丁二酰亚胺(NBS) 、 Na-borate 、 barium carbonate 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 0.5h， 生成 methyl 4-O-benzoyl-2,3-O-isopropylidene-α-D-rhamnopyranoside
  参考文献：
  名称：

  Thiem, Joachim; Gerken, Manfred; Bock, Klaus, Liebigs Annalen der Chemie, 1983, # 3, p. 462 - 470

  摘要：

  DOI：

文献信息

• Synthesis of a d-rhamnose branched tetrasaccharide, repeating unit of the O-chain from Pseudomonas syringae pv. Syringae (cerasi) 435
  作者：Emiliano Bedini、Antonella Carabellese、Maria Michela Corsaro、Cristina De Castro、Michelangelo Parrilli

  DOI：10.1016/j.carres.2004.06.010

  日期：2004.8

  The first synthesis of a d-rhamnose branched tetrasaccharide, corresponding to the repeating unit of the O-chain from Pseudomonas syringae pv. cerasi 435, as methyl glycoside is reported. The approach used is based on the synthesis of an opportune building-block, that is the methyl 3-O-allyl-4-O-benzoyl-alpha-D-rhamnopyranoside, which was then converted into both a glycosyl acceptor and two different

  d-鼠李糖支链四糖的首次合成，对应于丁香假单胞菌pv的O链重复单元。cerasi 435，因为报道了甲基糖苷。所使用的方法基于适当的构建基的合成，即甲基3-O-烯丙基-4-O-苯甲酰基-α-D-鼠李糖吡喃糖苷，然后将其转化为糖基受体和两个不同的保护基糖基三氯乙酰亚胺供体。这三种化合物的连续偶联提供了目标寡糖。所报道的合成对于进行重复单元的低聚反应也是有用的。
• Synthesis of a common polysaccharide antigen of Pseudomonas aeruginosa as the 6-aminohexyl glycoside
  作者：Yury E. Tsvetkov、Leon V. Backinowsky、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(89)85108-0

  日期：1989.10

  The synthesis is described of a tritylated 1,2-O-cyanoethylidene derivative (3) of the trisaccharide alpha-D-Rha-(1----2)-alpha-D-Rha-(1----3)-D-Rha. Triphenylmethylium perchlorate-catalysed polycondensation of 3 in the presence of 6-phthalimidohexyl 2,4-di-O-benzoyl-3-O-trityl-alpha-D-rhamnopyranoside followed by deprotection afforded the 6-aminohexyl glycoside of a D-rhamnan corresponding to a common

  描述了三糖α-D-Rha-（1 ---- 2）-α-D-Rha-（1 ---- 3）的三苯甲基化1,2-O-氰基亚乙基衍生物（3） -D-Rha。在6-邻苯二甲酰亚胺己基2,4-二-O-苯甲酰基-3-O-三苯甲基-α-D-鼠李吡喃糖苷的存在下，高氯酸三苯甲酯催化的3缩聚反应得到相应的D-鼠李糖苷的6-氨基己基糖苷铜绿假单胞菌的常见多糖抗原。
• Neue synthesen von aureolsäuretrisacchariden
  作者：Joachim Thiem、Manfred Gerken、Bernhard Schöttmer、Joachim Weigand

  DOI：10.1016/0008-6215(87)80139-8

  日期：1987.7

  the 3- C -methyl- d - arabino - and - d - ribo -glycosides with only little stereoselectivity. The glycosylation of benzyl 4- O -benzoyl-3- O -(4- O -benzoyl-2-bromo-2,6-dideoxy-β- d -glucopyranosyl)-2-bromo-2,6-dideoxy-β- d - glucopyranoside ( 14 ), selectively unprotected at the 3′ position, with 4 gave in excellent yield and stereoselectivity (β:α 10:1) preponderantly an all β- d -inked derivative

  摘要三氟甲基磺酸银促进了4-O-苯甲酰基-2-溴-2,6-二脱氧-3-O-甲酰基-α-d-吡喃葡萄糖基溴化物（4）与依苯辛基4-O-苯甲酰基-2-溴的缩合反应-2，6-二脱氧-β-d-吡喃葡萄糖苷（5）产生二糖，其在酯裂解后得到3'，4'-二醇组分（13）。通过N-碘丁二酰亚胺介导的D-Mycaral单乙酸酯与（13）苄基O-（4- O-乙酰基2,6-二脱氧-2-碘3- C 3-甲基-α-d吡喃并呋喃糖基-（1）的缩合→3）-获得O -2,6-二脱氧-β-d-阿拉伯-己吡喃糖基-（1→3）-4-O-苯甲酰基-2,6-二脱氧-β-d-阿拉伯糖-己吡喃糖苷（14）具有完全的区域特异性和立体特异性[仅α-d-（1″→3′）-键]，但产量适中；可以将其转化为光神霉素的EDC-三糖的异构体。 ，是苄基4- O-苯甲酰基-2的甲基支化基团，6-二脱氧-β-d-赤型-己基吡喃糖苷-3-ulose仅具有很
• Achiral Cyclodextrin Analogues
  作者：Peter R. Ashton、Stuart J. Cantrill、Giuseppe Gattuso、Stephan Menzer、Sergey A. Nepogodiev、Andrew N. Shipway、J. Fraser Stoddart、David J. Williams

  DOI：10.1002/chem.19970030818

  日期：1997.8

  AbstractThe synthesis of a new family of cyclodextrin (CD) analogues is described. This family consists of novel cyclic oligosaccharides built from monosaccharides that possess the same relative but opposite absolute (D‐ and L‐) configurations. The alternation of such D‐ and L‐ residues—specifically, D‐ and L‐rhamnose or D‐ and L‐mannose—in a macrocyclic structure results in Sn‐type symmetry and, consequently, optical inactivity. The synthesis of these cyclic oligosaccharides was achieved by an economical polycondensation/cycloglycosylation approach that relies on an appropriately‐derivatized disac‐charide monomer and that avoids the time‐consuming, and often low‐yielding, stepwise growth of long linear oligosaccharide precursors. In the cases reported, the key precursors are the disaccharide monomers 1‐RR and 1‐MM, which bear both a glycosyl donor (cyanoethylidene function) and a glycosyl acceptor (trity‐loxy group). These compounds are able to undergo Tr+‐catalyzed polycondensation which, under appropriate dilution conditions, can be terminated by cycloglycosyl‐ation. Thus, compound 1‐RR was converted into a range of protected cyclic rhamnooligosaccharides 15–19 in 64% overall yield. All these products, including the unique cyclic dodeca‐ and tetradecasaccharides 18 and 19, have been isolated by preparative HPLC. Unexpectedly, treatment of the manno analogue of the disaccharide 1‐RR (compound 1‐MM) under the same conditions produced only the cyclic hexasaccharide 28 and numerous apparently linear oligomers. Removal of the protecting groups from 16–19 afforded the free cyclic oligosaccharides 21–24, which exhibited the predicted zero optical rotation and very simple NMR spectra, indicating highly symmetrical structures. X‐ray crystallography reveals that in the solid state the cyclooctaoside 21 possesses a C2 symmetric structure, on account of a slight deformation of its cylindrical shape. The channel‐type crystal packing of molecules of 21 forms nanotubes with an internal diameter of around 1 nm. Conversely, the cyclic hexasaccharide 29 possesses a Ci symmetric solid‐state structure and its molecules pack to form a parquet‐like superstructure.
• Thiem, Joachim; Schoettmer, Bernhard, Angewandte Chemie, 1987, vol. 99, # 6, p. 591 - 592
  作者：Thiem, Joachim、Schoettmer, Bernhard

  DOI：——

  日期：——