摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

ethyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside | 132799-03-2

中文名称
——
中文别名
——
英文名称
ethyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside
英文别名
ethyl 4-O-benzyl-1-thio-alpha-l-rhamnopyranoside;(2S,3R,4S,5R,6S)-2-ethylsulfanyl-6-methyl-5-phenylmethoxyoxane-3,4-diol
ethyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside化学式
CAS
132799-03-2
化学式
C15H22O4S
mdl
——
分子量
298.403
InChiKey
SRGBKGZYKBEIAC-DJIJKHNZSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    88-90 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
  • 沸点:
    458.6±45.0 °C(Predicted)
  • 密度:
    1.22±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    1.6
  • 重原子数:
    20
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.6
  • 拓扑面积:
    84.2
  • 氢给体数:
    2
  • 氢受体数:
    5

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    • 1
    • 2

反应信息

点击查看最新优质反应信息

文献信息

  • Convergent synthesis of a pentasaccharide corresponding to the cell wall O-polysaccharide of enteropathogenic Escherichia coli O115
    作者:Monalisa Kundu、Arin Gucchait、Anup Kumar Misra
    DOI:10.1016/j.tet.2020.130952
    日期:2020.2
    orthogonal glycosylation approach has also been adopted for the preparation of a thioglycoside disaccharide derivative, which was used in the block synthesis. Perchloric acid supported over silica (HClO4–SiO2) has been used as a solid acid catalyst for the activation of glycosyl trichloroacetimidate derivative as well as in the thioglycoside activations. The d-galacturonic acid moiety in the molecules was incorporated
    已经使用收敛性嵌段糖基化策略以令人满意的产率合成了对应于肠致病性大肠杆菌O115的细胞壁O-多糖的五糖。合成策略涉及几个立体选择性糖基化步骤,其中值得一提的是C-3介导的氢键受体糖苷配基在β-3连接的L-鼠李糖基化反应中的远程吡啶啉基。正交糖基化方法也已经被用于制备代糖苷二糖衍生物,其被用于嵌段合成中。石上负载的高氯酸(HClO 4 -SiO 2)已被用作固体酸催化剂用于糖基三乙亚酸酯衍生物的活化以及糖苷的活化。的d在分子-galacturonic酸部分通过连接方式并入d在适当的糖基连接,随后后期TEMPO半乳糖单元介导的使用二乙酰氧基碘苯DAIB)的伯羟基的区域选择性氧化。所有中间糖基化都是高产率的,具有令人满意的立体结果。
  • Synthesis of 5-aminopentyl mono- to tri-saccharide haptens related to the species-specific glycopeptidolipids of Mycobacterium avium-intracellulare serovars 8 and 21
    作者:Thomas Ziegler
    DOI:10.1016/0008-6215(94)80062-6
    日期:1994.2
    The preparation of pyruvate acetal-containing 5-aminopentyl mono-, di-, and tri-saccharide fragments related to serovars 8 and 21 of the species-specific glycopeptidolipid of Mycobacterium avium-intracellulare is described. The saccharides were constructed by sequential coupling of the suitably protected 4,6-O-[(S)-1-methoxycarbonylethylidene]-D-glucopyranosyl trichloroacetimidates 6 and 7 to Z-protected
    描述了含丙酮酸缩醛的5-基戊基单糖,二糖和三糖片段的制备,所述片段与鸟分枝杆菌细胞内物种特异性糖肽脂质的血清型8和21有关。通过将适当保护的4,6-O-[(S)-1-甲氧基羰基亚乙基] -D-吡喃葡萄糖基三酰亚胺酸酯6和7依次偶联至Z-保护的5-戊醇来构建糖,从而得到血清素21单糖片段9解除封锁后;然后将其与2-O-苯甲酰基-4-O-苄基-1-代α-L-鼠李糖喃糖苷(18),分别得到相应的乙基1-代二糖21和23。随后N-代琥珀酰亚胺促进的后者与Z-保护的5-戊醇的偶联,然后将产物解封,分别得到相应的二糖片段26(血清素8)和27(血清素21)。用Z保护的5,基戊基3,4-二-O-苄基-6-脱氧-α-L-塔洛喃糖苷(28)缩合21,然后解封所得的三糖,得到血清素8片段5-基戊基O-( 4,6-O-[(S)-1-羧亚乙基] -3-O-甲基-β-D-吡喃葡萄糖基)-(1->
  • Chemical synthesis of the pyruvic acetal-containing trisaccharide unit of the species-specific glycopeptidolipid from Mycobacterium avium serovariant 8
    作者:Istv́n Bajza、János Kerékgyárto、János Hajkó、László Szilágyi、András Lipták
    DOI:10.1016/0008-6215(94)80059-6
    日期:1994.2
    functionalized, pyruvic acetal-containing haptenic trisaccharide, p-trifluoroacetamidophenyl 6-deoxy-2-O-(3-O-[4,6-O-(S)-(1-methoxycarbonylethylidene)-3-O-meth yl- beta-D-glucopyranosyl]-alpha-L-rhamnopyranosyl)-alpha-L-talopyranosid e (19), a component of the glycolipid from Mycobacterium avium serovar 8 was synthesized. For the preparation of the terminal pyruvic acetal-containing unit, benzyl 2-O-
    功能化的含丙酮酸缩醛的半抗原三糖对三乙酰胺基苯基6-脱氧-2-O-(3-O- [4,6-O-(S)-(1-甲氧羰基亚乙基)-3-O-甲基- β-D-葡萄糖喃糖基]-α-L-鼠李糖喃糖基)-α-L-talopyranoside(19),是来自鸟分枝杆菌血清型8的糖脂的组分。为了制备含丙酮酸缩醛的末端单元,将苄基2-O-苄基-3-O-甲基-β-D-吡喃葡萄糖苷(6)与2,2-二(乙基)丙酸甲酯(1)缩合。在SO2Cl2-CF3SO3H催化剂的存在下产生苄基2-O-苄基-4,6-O-(S)-(1-甲氧羰基亚乙基)-3-O-甲基-β-D-吡喃葡萄糖苷(7S)转化为适当取代的糖基供体2-O-乙酰基-4,6-O-(S)-(1-甲氧基羰基亚乙基)-3-O-甲基-α-α-D-吡喃葡萄糖基三酰亚胺酸酯(11)。二糖糖基受体对硝基苯基内酯3,4-O-亚苄基-6-脱氧-2-O-(2,4-二-O-苄基
  • Synthetic directions towards capsular polysaccharide of Streptococcus pneumoniae serotype 18C
    作者:Geeta Karki、Pintu Kumar Mandal
    DOI:10.1016/j.tetlet.2019.151153
    日期:2019.10
    compound after a series of functional group transformations. The synthetic method relies on the use of p-methoxybenzyl ether as an in situ-removable protecting group to reduce the number of reaction steps significantly. Here H2SO4-silica has been used successfully as a promoter for all glycosylation reaction. In addition, the synthetic target also contained a free amino group at its reducing end, facilitating
    已经开发了一种有效的合成策略,用于合成对应于肺炎链球菌血清型18C的荚膜多糖的三糖,四糖嵌段和五糖作为其2-基乙基糖苷。已采用一锅糖基化-脱保护,顺序糖基化策略来构建片段和五糖衍生物,然后在进行一系列官能团转化后将其转化为目标化合物。合成方法依赖于使用对甲氧基苄基醚作为可原位去除的保护基,以显着减少反应步骤。这里H 2 SO 4-二氧化硅已成功地用作所有糖基化反应的促进剂。此外,合成靶标在其还原端还包含一个游离基,有助于其与其他分子结合,用于各种生物学研究和应用。
  • Iodonium ion assisted synthesis of a common inner core trisaccharide fragment corresponding to the cell-wall phenolic glycolipid of Mycobacterium kansasii
    作者:Korien Zegelaar-Jaarsveld、Gijs A. van der Marel、Jacues H. van Boom
    DOI:10.1016/s0040-4020(01)89043-8
    日期:——
    The spacer containing trimer 4-(aminoethyl)phenyl 2,4-di-O-Me-3-O-[2-O-methyl-3-O-(4-O-acetyl-2-O-methyl-alpha-L-fucopyranosyl)-alpha-L-rhamnopyranosyl]-alpha-L-rhamnopyranoside (2) was prepared by stepwise extension of 4-[2-(benzyloxycarbonyl-amino)ethyl]phenyl 2,4-di-O-methyl-alpha-L-rhamnopyranoside (19) with property protected ethyl thioglycosides of L-rhamnose 8 and L-fucose 12 or 16 using iodonium ions as promotors. The resulting trimers 22 or 23 were deblocked in two steps to give homogeneous 2. Alternatively, fully protected trimer 22 was assembled by iodonium ion assisted condensation of the phenyl 1-thio-alpha-L-rhamnopyranoside 29 with 12 followed by extension of dimer 31 with 19.
查看更多