allyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside | 85207-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: allyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside
• 英文别名: 2,3,4,6-Di-O-isopropylidene-α-D-mannopyranoside；(1R,2S,6S,7S,9R)-4,4,12,12-tetramethyl-7-prop-2-enoxy-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecane
• CAS: 85207-15-4
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: OLFDWHBLAAGZGF-BNDIWNMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside 在 palladium dihydroxide 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 三甲基溴硅烷 、 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 、 potassium tert-butylate 、 水 、 氢气 、 高氯酸,吡啶 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 34.33h， 生成 [(2S,3S,4S,5R,6R)-5-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-tribenzoyloxyoxan-2-yl]oxy-3,4-dibenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]methylphosphonic acid
  参考文献：
  名称：

  Synthesis of β-d-Galp-(1→4)-α-d-Manp methanephosphonate, a substrate analogue for the elongating α-d-mannosyl phosphate transferase in the Leishmania

  摘要：

  An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00961-3
• 作为产物：
  描述：

  烯丙基2,3,4,6-四-O-乙酰基-ALPHA-D-吡喃甘露糖苷 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 allyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of β-d-Galp-(1→4)-α-d-Manp methanephosphonate, a substrate analogue for the elongating α-d-mannosyl phosphate transferase in the Leishmania

  摘要：

  An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00961-3

文献信息

• A new type of carbohydrate-containing synthetic antigen: Synthesis of carbohydrate-containing polysaccharide copolymers with the specificity of O:3 and O:4 factors of Salmonella
  作者：Nikolay K. Kochetkov、Boris A. Dmitriev、Anatoli Ya. Chernyak、Anatoli B. Levinsky

  DOI：10.1016/0008-6215(82)84022-6

  日期：1982.12

  The synthesis of a new type of synthetic antigen that contains no protein is described. Two linear polyacrylamide copolymers with carbohydrate branches were obtained via radical copolymerisation of the allyl glycosides of the oligosaccharide determinants O-beta-D-mannopyranosyl-(1----4)-O-alpha-L-rhamnopyranosyl-(1----3 )-beta-D- galactopyranose and O-3,6-dideoxy-alpha-D-xylo-hexopyranosyl-(1----3

  描述了不包含蛋白质的新型合成抗原的合成。通过寡糖决定簇O-β-D-甘露吡喃糖基-（1-4）-O-α-L-鼠李糖基-（1 --- -3）-β-D-吡喃半乳糖和O-3,6-dideoxy-alpha-D-xylo-hexopyranosyl-（1-3）-alpha-D-甘露吡喃糖与丙烯酰胺。这些共聚物含有30％的碳水化合物，分子量超过100道尔顿，具有沙门氏菌的基团特异性E和B。
• A new type of carbohydrate-containing synthetic antigen: Synthesis of carbohydrate-containing polyacrylamide copolymers having the specificity of O:3 and O:4 factors of Salmonella
  作者：Antoliy Ya. Chernyak、Anatoliy B. Levinsky、Boris A. Dmitriev、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(84)85334-3

  日期：1984.6

  The synthesis of a new type of synthetic antigen that contains no protein is described. Two linear polyacrylamide copolymers with carbohydrate branches were obtained via radical copolymerisation of the allyl glycosides of the oligosaccharide determinants O-beta-D-mannopyranosyl-(1----4)-O-alpha-L-rhamnopyranosyl-(1----3 )-beta-D- galactopyranose and O-3,6-dideoxy-alpha-D-xylo-hexopyranosyl-(1----3

  描述了不包含蛋白质的新型合成抗原的合成。通过寡糖决定簇O-β-D-甘露吡喃糖基-（1-4）-O-α-L-鼠李糖基-（1 ---）的烯丙基糖苷的自由基共聚反应，获得了两个带有碳水化合物支链的线性聚丙烯酰胺共聚物。 -3）-β-D-吡喃半乳糖和O-3,6-dideoxy-alpha-D-xylo-hexopyranosyl-（1-3）-alpha-D-甘露吡喃糖与丙烯酰胺。这些共聚物含有30％的碳水化合物，分子量超过100道尔顿，具有沙门氏菌的基团特异性E和B。
• Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives
  作者：Johannes Kunig、Peter Lönnecke、Evamarie Hey-Hawkins

  DOI：10.1016/j.carres.2011.03.035

  日期：2011.7

  Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives were prepared and fully characterized. The procedure is generally applicable to monosaccharides and thus facilitates access to differently substituted glycosidic precursors.

  制备对映体纯的3-羟丙基二异亚丙基甘露糖衍生物并充分表征。该方法通常适用于单糖，因此有助于获得不同取代的糖苷前体。
• ‘Sugaring’ carbosilane dendrimers via hydrosilylation
  作者：Mike M.K Boysen、Thisbe K Lindhorst

  DOI：10.1016/s0040-4020(03)00458-7

  日期：2003.5

  into dendritic carbosilane structures were explored. Pathway one utilised alcoholysis of a chlorosilane with a protected hydroxyethyl glycoside resulting in Si–O linkages. Pathway two proceeds via a hydrosilylation reaction of a protected allyl glycoside with a carbosilane containing Si–H end groups in the presence of a platinum catalyst, thus leading to Si–C linked structures.

  探索了将碳水化合物衍生物引入树状碳硅烷结构的两种新途径。途径之一利用了氯硅烷与保护的羟乙基糖苷的醇解作用，从而形成了Si-O键。途径二是通过在铂催化剂存在下，受保护的烯丙基糖苷与含Si-H端基的碳硅烷的硅烷化反应进行的，从而导致Si-C连接的结构。
• Synthesis of propyl 4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-2,3-di-O-methyl-α-d-rhamnopyranoside
  作者：Jill Gigg、Roy Gigg、Sheila Payne、Robert Conant

  DOI：10.1016/s0008-6215(00)90758-4

  日期：1985.8

  Abstract Partial hydrolysis of allyl 2,3:4,6-di- O -isopropylidene-α- d -mannopyranoside gave allyl 2,3- O -isopropylidene-α- d -mannopyranoside which was converted into allyl 2,3- O -isopropylidene-α- d -rhamnopyranoside by reduction of the 6- O -tosyl derivative with lithium aluminium hydride. Condensation of allyl 2,3- O -isopropylidene-α- d -rhamnopyranoside with 2,4-di- O -acetyl-3,6-di- O -methyl-α-

  摘要2,3：4,6-二-O-异亚丙基-α-d-甘露吡喃糖苷烯丙基的部分水解得到烯丙基2,3-O-异亚丙基-α-d-甘露吡喃糖苷，其转化为烯丙基2,3-O-通过用氢化锂铝还原6-O-甲苯磺酰基衍生物，得到异亚丙基-α-d-鼠李吡喃糖苷。汞存在下，2,3-O-异亚丙基-α-d-鼠李吡喃糖苷烯丙基与2,4-二-O-乙酰基-3,6-二-O-甲基-α-d-吡喃葡萄糖酰氯的缩合反应（II）氰化物得到结晶的β-连接的二糖，将其转化为标题化合物。