methyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside | 25019-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside
• 英文别名: methyl 4-O-benzyl-2,3-O-isopropylidine-α-L-rhamnopyranoside；(3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-7-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 25019-68-5
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: WUHGTVIXLTZESM-RBRCJPGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 在 吡啶 、 咪唑 、 palladium dihydroxide 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 四丁基碘化铵 、 二正丁基氧化锡 、 溶剂黄146 、 硫代氯甲酸苯酯 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-Butyl-((2S,3S,4S)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane
  参考文献：
  名称：

  Practical synthesis of oligosaccharides. Partial synthesis of avermectin B1a

  摘要：

  DOI：

  10.1021/ja00327a021
• 作为产物：
  描述：

  甲基-Alpha-D-吡喃鼠李糖苷 在 calcium sulfate 、 氢氧化钾 、 copper(II) sulfate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  Batavyal, Lakshmi; Roy, Nirmolendu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 5, p. 499 - 500

  摘要：

  DOI：

文献信息

• Synthesis and hydrogenolysis of the methylene, ethylidene, isopropylidene, and diastereoisomeric 1-phenylethylidene acetals of β-l-arabino- and α-l-rhamnopyranoside derivatives
  作者：András Lipták、Zoltán Szurmai、V.Anna Oláh、János Harangi、Lajos Szabó、Pál Nánási

  DOI：10.1016/0008-6215(85)85218-6

  日期：1985.4

  diastereoisomers of 1-phenylethylidene acetals (acetophenone acetals) of methyl and benzyl β- l -arabinopyranoside and α- l -rhamnopyranoside were prepared. Acetal-exchange reactions gave only the endo -phenyl isomers; their 2- O - and 4- O -acetyl derivatives were isomerised into the exo -phenyl compounds. 1 H-N.m.r. data were used to determine the absolute configuration at the acetal carbon atom in these compounds

  摘要分别制备了甲基和苄基β-1-L-阿拉伯吡喃糖苷和α-1-R-鼠李糖吡喃糖苷的1-苯基亚乙基缩醛（苯乙酮缩醛）的非对映异构体。缩醛交换反应仅产生内-苯基异构体。它们的2-O-和4-O-乙酰基衍生物被异构化为外苯基化合物。1 HN.mr数据用于确定这些化合物中乙缩醛碳原子的绝对构型。与内苯基异构体相比，外苯基异构体的甲基质子在较低的场共振。各种亚甲基，亚乙基和异亚丙基衍生物的氢解反应得到轴向醚。苯乙酮衍生物的内-苯基异构体还产生了两种非对映异构形式的轴向1-苯基乙基醚。
• Synthesis of disaccharide methyl glycosides related to the polysaccharide from Klebsiella serotype 40 and a study of their inhibition in the precipitin reaction
  作者：Usha B. Maddali、Asim K. Ray、Nirmolendu Roy

  DOI：10.1016/0008-6215(90)80085-h

  日期：1990.12

  Galp (4), beta-L-Rhap-(1----3)-beta-D-Galp (5), beta-D-Galp-(1----2)-alpha-L-Rhap (6), and beta-D-GlcpA-(1----2)-alpha-L-Rhap (7) have been synthesised and their inhibition reactions in the Klebsiella serotype 40 immune system have been studied. The results obtained accord with only one of two structures proposed for the repeating unit of the K40 antigen.

  alpha-D-Manp-（1 ---- 4）-alpha-L-Rhap（3），alpha-L-Rhap-（1 ---- 3）-beta-D-Galp（4 ），beta-L-Rhap-（1 ---- 3）-beta-D-Galp（5），beta-D-Galp-（1 ---- 2）-alpha-L-Rhap（6），合成了β-D-GlcpA-（1 ---- 2）-α-L-Rhap（7）并研究了它们在克雷伯菌血清型40免疫系统中的抑制反应。获得的结果仅与为K40抗原的重复单位提出的两个结构之一一致。
• 10.1021/acs.orglett.4c01367
  作者：Suwa, Tomoya、Sasaki, Makoto、Umehara, Atsushi

  DOI：10.1021/acs.orglett.4c01367

  日期：——

  The total synthesis of marine macrolide glycoside (−)-irijimaside A is described. Key to the synthesis is the convergent fragment assembly enabled by nickel/zirconocene-mediated one-pot reductive ketone coupling. At the last stage of the synthesis, Stille coupling and glycosylation led to the first total synthesis of (−)-irijimaside A.

  描述了海洋大环内酯糖苷 (-)-irijimaside A 的全合成。合成的关键是通过镍/二茂锆介导的一锅还原酮偶联实现聚合片段组装。在合成的最后阶段，Stille 偶联和糖基化导致了 (−)-irijimaside A 的首次全合成。
• Induction of a Preferred Sense of Twist in Flexible Diphenyls by Carbohydrate Scaffolds. Synthesis of Two “Naked” Ellagitannin Analogous
  作者：Giuseppe Capozzi、Cinzia Ciampi、Giovanna Delogu、Stefano Menichetti、Cristina Nativi

  DOI：10.1021/jo010522c

  日期：2001.12.1

  The synthesis of "naked" ellagitannin analogues 1 and 2, having a preferred sense of twist of the diphenyl moiety, with a rhamnose and a glucose template, is reported. A clear induction in the chirality of the diphenyl moiety, mediated through a 10-membered ring via ester linkages, was observed. The chiral scaffold of glucose (diequatorial 2,3-hydroxyl groups) exerts a remarkable stronger atropdiastereoselective effect onto the diphenoyl group than the rhamnose ring (axial-equatorial 2,3-hydroxyl groups), according to the Schmidt-Haslam hypothesis.
• Mukherjee, Atreyee; Roy, Nirmolendu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 8, p. 726 - 728
  作者：Mukherjee, Atreyee、Roy, Nirmolendu

  DOI：——

  日期：——