Ethyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside | 145124-97-6

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside
• 英文别名: (3aS,4R,6R,7R,7aS)-4-ethylsulfanyl-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 145124-97-6
• 化学式: C₁₁H₂₀O₄S
• 分子量: 248.343
• InChiKey: MFKXLPULGXBOJW-FHNUBNKASA-N

物化性质

• 沸点：
  375.6±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium hydride 、 二正丁基氧化锡 、 碳酸氢钠 、 溶剂黄146 、 cesium fluoride 作用下， 以 乙醚 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.25h， 生成 4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2-O-chloroacetyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside
  参考文献：
  名称：

  Iodonium ion-assisted synthesis of a tetrameric fragment corresponding to the cell wall phenolic glycolipids of Mycobacterium kansasii serovar I

  摘要：

  Two procedures are described towards the assembly of the tyramine spacer-containing tetramer 5, a derivative of the phenolic glycolipid of Mycobacterium kansasii serovar I. First, iodonium ion-mediated glycosylation of trimeric acceptor 2a with D-rhamnopyranoside donor 10 gave fully protected tetramer 17. Selective removal of the chloroacetyl group of 17, subsequent deoxygenation and removal of the protective groups, led to target 5. The potential occurrence of double stereodifferentiation (DSD) was examined by condensation of L-fucopyranoside model acceptor 14 with both the enantiomeric rhamnopyranoside donors 10 and 13. The second procedure involves elongation of trimeric acceptor 2b with 6-deoxy-D-glucopyranoside 28. Desulfurisation of the resulting tetrameric fragment 36 followed by hydrogenation of 37 gave 38, the phenylacetyl (PhAc) of which was enzymatically removed to yield target tetramer 5.

  DOI：

  10.1016/0040-4020(96)00035-x
• 作为产物：
  描述：

  ethyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 在 palladium on activated charcoal 咪唑 、 氢气 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 96.0h， 生成 Ethyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Tetrasaccharide Repeating Unit of the O‐Antigen from Enterohemorrhagic Escherichia coli O157 in the form of its 2‐(trimethylsilyl)ethyl Glycoside

  摘要：

  Two alpha-linked disaccharide derivatives, ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl-(1 -> 2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-alpha-D-mannopyranoside (10) and 2-(trimethylsilyl)ethyl 3-O-acetyl-4-O-benzoyl-2-O-benzyl-alpha-L-fucopyranosyl-(1 -> 4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-beta-D-glucopyranoside (16), were prepared from appropriate monosaccharide synthons. The disaccharide 16 was deacetylated and debenzoylated to afford the acceptor 17, which was allowed to react with the donor 10 to afford a tetrasaccharide derivative 18. This tetrasaccharide was transformed in three steps into 21, the desired repeating unit of the antigen from enterohemorrhagic E. coli type O157.

  DOI：

  10.1080/07328300500495878

文献信息

• Chemical Synthesis Elucidates the Key Antigenic Epitope of the Autism‐Related Bacterium <i>Clostridium bolteae</i> Capsular Octadecasaccharide
  作者：Juntao Cai、Jing Hu、Chunjun Qin、Lingxin Li、Dacheng Shen、Guangzong Tian、Xiaopeng Zou、Peter H. Seeberger、Jian Yin

  DOI：10.1002/anie.202007209

  日期：2020.11.9

  spectrum disorder (ASD). To create vaccines against C. bolteae, it is important to identify exact protective epitopes of the immunologically active capsular polysaccharide (CPS). Here, a series of C. bolteae CPS glycans, up to an octadecasaccharide, was prepared. Key to achieving the total syntheses is a [2+2] coupling strategy based on a β‐d‐Rhap‐(1→3)‐α‐d‐Manp repeating unit that in turn was accessed by

  肠道病原体梭状芽胞杆菌与自闭症谱系障碍（ASD）的发作有关。要创建针对螺栓念珠菌的疫苗，重要的是要确定具有免疫活性的荚膜多糖（CPS）的确切保护表位。在这里，制备了一系列的紫花C. CPS聚糖，直至十八糖。键实现的全合成是[2 + 2]根据一个β-偶联策略d -RHA p - （1→3）-α- d -Man p重复单元，其又被立体选择性β-访问d鼠李糖基化。4,6‐ O亚苄基诱导的构象锁定是形成β- d-甘露糖型糖苷的强大策略。通过Swern氧化和硼氢化物还原有效地实现了基于C2差向异构化的β- d-奎奴诺酮的间接策略。顺序糖基化，区域选择性和整体脱保护产生了二糖和四糖，直至十八糖。对灭活的克雷伯氏菌进行免疫的兔血清的糖微阵列分析显示对二糖和四糖有体液免疫反应，但没有更长的序列。四糖可能是设计抗克氏梭菌的糖结合疫苗的关键主题。
• Synthesis of p-trifluoroacetamidophenyl 6-deoxy-2-O-3-O- [2-O-methyl-3-O-(2-O-methyl-α-d-rhamnopyranosyl)- α-l-fucopyranosyl]-α-l-rhamnopyranosyl-α-l- talopyranoside: a spacer armed tetrasaccharide glycopeptidolipid antigen of Mycobacterium avium serovar 20
  作者：János Kerékgyártó、Zoltán Szurmai、András Lipták

  DOI：10.1016/0008-6215(93)80060-r

  日期：1993.7

  O -benzyl-1-thio-α- l -rhamnopyranoside ( 9 ), affording the same disaccharide derivative 8 . Deacetylation of 8 gave crystalline 17 . Condensation of 17 with both fucosyl donors 15 and 16 yielded the same trisaccharide derivative 18 stereoselectively. Compound 18 was also prepared by the coupling of 4 with disaccharide glycosyl donor 20 . After deacetylation of 18 (→ 34 ), methyl triflate-promoted

  摘要报道了标题四糖苷38的合成。对-硝基苯基内酯-3,4- O-亚苄基-6-脱氧-α-1-塔拉吡喃糖苷（4，3-O-乙酰基-2,4-二-O-苄基-α-1-鼠李糖基吡喃糖基三氯乙酰亚氨酸盐（7）甲基3-O-乙酰基-4-O-苄基-2-O-甲基-1-硫代-β-1-呋喃核糖苷（15）3-O-乙酰基-4-O-苄基-2-O-甲基-制备了α-1-呋喃核糖基溴化物（16）和乙基3-O-乙酰基-4-O-苄基-2-O-甲基-1-硫代-α-d-鼠李糖吡喃糖苷（33）作为化合物4。用亚氨酸酯7以及3-- O-乙酰基-2,4-二-O-苄基-1-硫代-α-1-L-鼠李糖吡喃糖苷（9）进行糖基化，得到相同的二糖衍生物8。图17.将17与岩藻糖基供体15和16两者缩合，立体选择性地产生相同的三糖衍生物18。还通过将4与二糖糖基供体20偶联来制备化合物18。18（→34）脱乙酰基后，三氟甲磺酸甲酯与化合物33的糖基化反应产