(1R,3S,4R,5S,8S)-4,8-bis(benzyloxy)-3-methoxy-2,6-dioxabicyclo[3.2.1]octane | 50721-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3S,4R,5S,8S)-4,8-bis(benzyloxy)-3-methoxy-2,6-dioxabicyclo[3.2.1]octane
• 英文别名: methyl 3,6-anhydro-2,4-di-O-benzyl-α-D-galactopyranoside；(1R,3S,4R,5S,8S)-3-methoxy-4,8-bis(phenylmethoxy)-2,6-dioxabicyclo[3.2.1]octane
• CAS: 50721-02-3
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: ZMLCDSNHQQKQAH-IFLJBQAJSA-N

物化性质

• 沸点：
  477.7±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 在 potassium thioacetate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (1R,3S,4R,5S,8S)-4,8-bis(benzyloxy)-3-methoxy-2,6-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  亲核取代反应首次合成仲糖磺酸

  摘要：

  通过三氟甲磺酸酯介导的亲核取代反应，或者用NaHSO 3制备α-d-葡萄糖基和α-d-吡喃半乳糖苷甲基的4-deoxy-4- C-磺酸和6-deoxy-6- C-磺酸衍生物。3或使用AcSK。甲基三氟甲磺酸酯的酯2,3,4-三ø苄基1，甲基2,3,6-三- ö苄基α-d-D-吡喃葡萄糖苷9和甲基2,3,6-三- ø -苄基-α-d-吡喃半乳糖苷5提供了甲基6-脱氧-6- C-磺基-α-d-吡喃吡喃糖苷4，甲基4-脱氧-4- C-磺基-α-d-吡喃半乳糖苷12和α-d-吡喃葡萄糖苷8。甲基2,3,4-三-O-苄基-α-d-吡喃半乳糖苷13的三氟甲磺酸衍生物得到甲基3,6-脱水-2,4-二-O-苄基-α-d-吡喃半乳糖苷14。通过使用3，4- O-异亚丙基缩醛保护防止甲基3，6-脱水衍生物的形成以获得甲基6-脱氧-6- C-磺基-α-d-吡喃半乳糖苷19。该研究的目的是在糖胺聚糖的重复寡糖单元

  DOI：

  10.1016/j.tetlet.2003.11.025

文献信息

• Synthesis of methyl 2,3-O-glycopyranosylidene-α-d-mannopyranosides having various substituents
  作者：Juji Yoshimura、Katsuji Asano、Kazuyuki Umemura、Shigeomi Horito、Hironobu Hashimoto

  DOI：10.1016/0008-6215(83)84016-6

  日期：1983.9

  title compounds were obtained by condensation of d -glucono-, d -galactono-, or l - glycero - d - gluco -heptono-1,5-lactones with methyl 2,3-di- O -(trimethylsilyl)-α- d -mannopyranosides having various substituents on C-4 and C-6, in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst. Except for a 6-acetoxyl group on a lactone component and a ( tert -butyldiphenylsiloxy) group

  摘要标题化合物是通过将d-葡萄糖酸-，d-半乳糖基-或l-甘油-d-葡萄糖-庚基-1,5-内酯与2,3-二甲基O-（三甲基甲硅烷基）-α缩合而获得的。在三甲基甲硅烷基三氟甲磺酸盐作为催化剂的存在下，在C-4和C-6上具有各种取代基的-d-甘露吡喃糖苷。除了内酯组分上的6-乙酰氧基和（叔丁基二苯基甲硅烷氧基）基团外，常用的C-取代基，例如苄氧基，烯丙氧基，叠氮基，酰氧基，（甲硫基）甲氧基和甲氧基，均不能阻止这种情况的发生。缩合。
• RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo
  作者：Takuya Tashiro、Ryusuke Nakagawa、Sayo Inoue、Masao Shiozaki、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.tetlet.2008.09.074

  日期：2008.11

  RCAI-61, the 6'-O-methylated analog of KRN7000, and six other analogs with modified 6'-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl alpha-D-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl beta-L-arabinopyranoside. Bioassay showed RCAI-61 to be a Much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-gamma in vivo. (C) 2008 Elsevier Ltd. All rights reserved.
• RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo
  作者：Takuya Tashiro、Ryusuke Nakagawa、Tomokuni Shigeura、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.bmc.2013.03.028

  日期：2013.6

  We synthesized ten new analogs of 6'-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by alpha-selective galactosylation of ceramide 9 with the 6-modified D-galactopyranosyl fluorides (8a-8f) or L-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6'-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-gamma even at a low concentration in mice in vivo. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and conformational studies of carrabiose and its 4′-sulphate and 2,4′-disulphate
  作者：Enrique Parra、Hugo-Norberto Caro、Jesús Jiménez-Barbero、Manuel Martín-Lomas、Manuel Bernabé

  DOI：10.1016/0008-6215(90)80087-j

  日期：1990.12

  Methyl alpha-carrabioside (13), and its 4-sulphate (19) and 2,4-disulphate (20) have been synthesised via glycosylation of methyl 3,6-anhydro-2-O-benzyl-alpha-D-galactopyranoside with 2,3,6-tri-O-acetyl-4-O-benzyl-beta-D-galactopyranosyl bromide and subsequent partial or complete debenzylation, sulphation, and deprotection of the resulting disaccharide derivatives. Conformational studies have been carried out on 13, 19, and 20 on the basis of 1D and 2D 1H-n.m.r. spectroscopy and molecular mechanics calculations.
• Borbas, Aniko; Biro, Andrea; Liptak, A., ACH - Models in Chemistry, 1994, vol. 131, # 3-4, p. 455 - 466
  作者：Borbas, Aniko、Biro, Andrea、Liptak, A.

  DOI：——

  日期：——