Phenyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside | 439914-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside
• 英文别名: Phenyl 2,3-O-isopropylidene-1-thio-alpha-D-rhamnopyranoside；(3aS,4R,6R,7R,7aS)-2,2,6-trimethyl-4-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 439914-99-5
• 化学式: C₁₅H₂₀O₄S
• 分子量: 296.387
• InChiKey: YOEZBAWYJHTIPW-QKGWFMCXSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  448.2±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  Phenyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 [(2S,3R,4S,5R,6R)-2-[[(3aS,4R,6R,7R,7aS)-2,2,6-trimethyl-4-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-6-methyl-5-phenylmethoxy-3-phenylsulfanyloxan-4-yl] methylsulfanylformate
  参考文献：
  名称：

  Efficient Synthesis of the Hexasaccharide Fragment of Landomycin A:  Using Phenyl 2,3-O-Thionocarbonyl-1-thioglycosides as 2-Deoxy-β-glycoside Precursors

  摘要：

  [GRAPHICS]The beta-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-Xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.

  DOI：

  10.1021/ol0259286
• 作为产物：
  描述：

  [(3aS,4R,6R,7R,7aR)-2,2-dimethyl-4-phenylsulfanyl-7-tri(propan-2-yl)silyloxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]methyl 4-methylbenzenesulfonate 在 lithium aluminium tetrahydride 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 Phenyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside
  参考文献：
  名称：

  (-)-Sodarin的合成

  摘要：

  (-)-sordarin (1) 的首次全合成利用以下关键反应完成：(i) Ag(I)-催化氧化自由基环化环丙醇衍生物生成双环 [5.3.0]decan-3-一具骷髅；(ii) Pd(0)-催化的分子内烯丙基化反应产生完整的双环[2.2.1]heptan-2-one骨架sordaricin (2)；(iii) 通过组合使用 OsO(4) 和 PhB(OH)(2) 选择性地二羟基化末端烯烃；(iv) 通过 4-甲氧基苯甲酰基的 1,3-嵌合辅助作用进行 β(1,2-顺式)-选择性糖苷化。

  DOI：

  10.1021/ja060408h

文献信息

• 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
• Recent advances in the synthesis of 2-deoxy-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.carres.2009.07.013

  日期：2009.10

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.
• Goemez, Ana M.; Casillas, Marta; Rodriguez, Benjamin, ARKIVOC, 2010, vol. 2010, # 3, p. 288 - 302
  作者：Goemez, Ana M.、Casillas, Marta、Rodriguez, Benjamin、Valverde, Serafin、Loepez, J. Cristoebal

  DOI：——

  日期：——
• Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor
  作者：Hasnah Osman、David S. Larsen、Jim Simpson

  DOI：10.1016/j.tet.2009.03.092

  日期：2009.5

  1,3-Di-O-acetyl-4-O-benzyl-2,6-dideoxy-D-arabinopyranose (11) was synthesised from thiophenyl alpha-D-mannopyranoside (21) in an eight-step sequence. Tosylation of 21 and subsequent reaction with 2,2-dimethoxypropane gave tosylate 22, which upon treatment with lithium aluminium hydride furnished 6-deoxy glycoside 24 and by-product thiophenyl 6-deoxy-2-O-isopropyl-alpha-D-arabinopyranoside. The X-ray crystal structure of the latter was determined. Benzylation of the 4-hydroxyl group of 24 and Subsequent protecting group manipulation gave D-rhamnosyl bromide 29, which on treatment with zinc-copper couple gave the orthogonally protected D-rhamnal 30. Triphenylphosphine hydrogen bromide catalysed addition of acetic acid to 30 furnished the target molecule 11. The scandium(III) triflate promoted reaction of 11 and 2-naphthol gave the corresponding C-glycoside 36 in 86% yield. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.