3,4,6-tri-O-benzoyl-α-D-mannopyranose 1,2-(allyl orthoacetate) | 324041-18-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,6-tri-O-benzoyl-α-D-mannopyranose 1,2-(allyl orthoacetate)
• 英文别名: 3,4,6-tri-O-benzoyl-1,2-O-allyloxyethylidene-β-D-mannopyranose；3,4,6-tri-O-benzoyl-1,2-O-allyloxyethylidene-β-D-mannopranose；[(3aS,5R,6R,7S,7aS)-6,7-dibenzoyloxy-2-methyl-2-prop-2-enoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl benzoate
• CAS: 324041-18-1
• 化学式: C₃₂H₃₀O₁₀
• 分子量: 574.584
• InChiKey: MSPHPUHUEZWRRR-IKWLHOGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzoyl-α-D-mannopyranose 1,2-(allyl orthoacetate) 在 三氟甲磺酸三甲基硅酯 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 allyl (3,4,6-tri-O-benzoyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  α-Manp-（1→2）-α-Manp-（1→3）-α-Manp-（1→3）-Manp，大肠杆菌O9a的四糖重复单元和α-Manp-（1的合成→2）-α-Manp-（1→2）-α-Manp-（1→3）-α-Manp-（1→3）-Manp，大肠杆菌O9和Klebsiella O3的五糖重复单元

  摘要：

  摘要大肠杆菌O9a的四糖重复单元，α-d -Man p-（1→2）-α-d -Man p-（1→3）-α-d -Man p-（1→3）-d -Man p和大肠杆菌O9和克雷伯菌O3的五糖重复单元，α-d -Man p-（1→2）-α-d-Man p-（1→2）-α-d -Man p合成了-（1→3）-α-d-Manp-（1→3）-d-Man p作为甲基糖苷。因此，对-甲氧基苯基α-d-甘露吡喃糖苷经由二丁基锡中间体的选择性3-O-烯丙基化以良好的产率得到了对-甲氧基苯基3-O-烯丙基-α-d-甘露吡喃糖苷（2）。苯甲酰化（→3），然后除去1- O-甲氧基苯基（→4），然后进行三氯乙酰亚胺化，得到3- O-烯丙基-2,4,6-三-O-苯甲酰基-α-d-甘露酰吡喃糖基三氯乙酰胺酸酯（5 ）。5与甲基4,6-O-亚苄基-α-d-甘露吡喃糖苷（6）缩合选择性地提供（1→3）-连接的二糖7。7的苄基

  DOI：

  10.1016/s0008-6215(02)00011-3
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 吡啶 、 甲醇 、 sodium hydroxide 、 2,4-二甲基吡啶 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 生成 3,4,6-tri-O-benzoyl-α-D-mannopyranose 1,2-(allyl orthoacetate)
  参考文献：
  名称：

  高效合成在 HIV 糖蛋白 gp 120 上表达的 N-聚糖的甘露糖九糖

  摘要：

  通过 TMSOTf 促进四糖-4,6-二醇受体与五糖供体的选择性 6-糖基化，然后进行脱保护，实现了表达在 HIV 蛋白 gp 120 上的甘露糖非异构体的高效简洁合成。五糖是通过 1,2-O-ethylidene-β-d-mannopyranose 与 2-O-acetyl-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate 的选择性 3,6-二糖基化构建的，而四糖则是通过烯丙基 4,6-O-benzilidene-β-d-mannopyranose-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate 的选择性 3-O-糖基化获得的、6-O-二苯甲酰基-δ-d-吡喃甘露糖苷与 2,3,4,6-四-O-苯甲酰基-δ-d-吡喃甘露糖基-(1→2)-3,4,6-三-O-苯甲酰基-δ-d-吡喃甘露糖基-(1→2)-3,4,6-三-O-苯甲酰基-δ-d-吡喃甘露糖基三氯亚氨酸酯进行选择性 3-O-糖基化反应得到四糖。

  DOI：

  10.1055/s-2001-16062

文献信息

• Synthesis of α-Manp-(1→2)-α-Manp-(1→3)-α-Manp-(1→3)-Manp, the tetrasaccharide repeating unit of Escherichia coli O9a, and α-Manp-(1→2)-α-Manp-(1→2)-α-Manp-(1→3)-α-Manp-(1→3)-Manp, the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3
  作者：Langqiu Chen、Yuliang Zhu、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00011-3

  日期：2002.3

  3- O -allyl-2,4,6-tri- O -benzoyl-α- d -mannopyranosyl trichloroacetimidate ( 5 ). Condensation of 5 with methyl 4,6- O -benzylidene-α- d -mannopyranoside ( 6 ) selectively afforded the (1→3)-linked disaccharide 7 . Benzoylation of 7 , debenzylidenation, benzoylation, and deallylation gave methyl 2,4,6-tri- O -benzoyl-α- d -mannopyranosyl-(1→3)-2,4,6-tri- O -benzoyl-α- d -mannopyranoside ( 11 ) as the

  摘要大肠杆菌O9a的四糖重复单元，α-d -Man p-（1→2）-α-d -Man p-（1→3）-α-d -Man p-（1→3）-d -Man p和大肠杆菌O9和克雷伯菌O3的五糖重复单元，α-d -Man p-（1→2）-α-d-Man p-（1→2）-α-d -Man p合成了-（1→3）-α-d-Manp-（1→3）-d-Man p作为甲基糖苷。因此，对-甲氧基苯基α-d-甘露吡喃糖苷经由二丁基锡中间体的选择性3-O-烯丙基化以良好的产率得到了对-甲氧基苯基3-O-烯丙基-α-d-甘露吡喃糖苷（2）。苯甲酰化（→3），然后除去1- O-甲氧基苯基（→4），然后进行三氯乙酰亚胺化，得到3- O-烯丙基-2,4,6-三-O-苯甲酰基-α-d-甘露酰吡喃糖基三氯乙酰胺酸酯（5 ）。5与甲基4,6-O-亚苄基-α-d-甘露吡喃糖苷（6）缩合选择性地提供（1→3）-连接的二糖7。7的苄基
• A FACILE SYNTHESIS OF MANNOSE TRI- AND TETRASACCHARIDE REPEATING UNITS OF FUNGAL CELL-WALL POLYSACCHARIDE FROM<i>MICROSPORUM</i>AND<i>TRYCHOPHYTON</i>SPECIES
  作者：Yuliang Zhu、Fanzuo Kong

  DOI：10.1081/scc-120003613

  日期：2002.1

  ABSTRACT A facile synthesis of the trisaccharide α-D-mannopyranosyl-(1→2)-α-D-mannopyranosyl-(1→6)-α-D-mannopyranose and the tetrasaccharide α-D-mannopyranosyl-(1→2)-α-D-mannopyranosyl-(1→6)-α-D-mannopyranosyl-(1→6)-D-mannopyranose, the repeating units of fungal cell-wall polysaccharide from Microsporum gypseum and Trychophyton, was achieved using α-(1→2)-linked disaccharide imidate as the donor. The

  摘要 三糖 α-D-吡喃甘露糖基-(1→2)-α-D-吡喃甘露糖基-(1→6)-α-D-吡喃甘露糖和四糖 α-D-吡喃甘露糖基-(1→2) 的简便合成-α-D-吡喃甘露糖基-(1→6)-α-D-吡喃甘露糖基-(1→6)-D-吡喃甘露糖是来自石膏小孢子菌和毛癣菌的真菌细胞壁多糖的重复单元，使用α-( 1→2)-连接的二糖亚胺酸酯作为供体。二糖亚氨酸酯由 3,4,6-tri-O-benzoyl-1,2-O-allyloxyethylidene-β-D-mannopyranose 的自缩合制备。
• Zhu; Kong, Synlett, 2000, # 12, p. 1783 - 1787
  作者：Zhu、Kong

  DOI：——

  日期：——
• Highly Efficient Synthesis of the Mannose Nonasaccharide of the N-Glycan Expressed on the HIV Glycoprotein gp 120
  作者：Yuliang Zhu、Fanzuo Kong

  DOI：10.1055/s-2001-16062

  日期：——

  A highly concise and effective synthesis of the mannose nonasaccharide of the glycan expressed on the HIV protein gp 120 was achieved via TMSOTf promoted selective 6-glycosylation of a tetrasaccharide 4,6-diol acceptor with a pentasaccharide donor followed by deprotection. The pentasaccharide was constructed by selective 3,6-diglycosylation of 1,2-O-ethylidene-β-d-mannopyranose with 2-O-acetyl-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate while the tetrasaccharide was obtained by selective 3-O-glycosylation of allyl 4,6-O-benzilidene-α-d-mannopyranoside with 2,3,4,6-tetra-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl trichloroimidate.

  通过 TMSOTf 促进四糖-4,6-二醇受体与五糖供体的选择性 6-糖基化，然后进行脱保护，实现了表达在 HIV 蛋白 gp 120 上的甘露糖非异构体的高效简洁合成。五糖是通过 1,2-O-ethylidene-β-d-mannopyranose 与 2-O-acetyl-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate 的选择性 3,6-二糖基化构建的，而四糖则是通过烯丙基 4,6-O-benzilidene-β-d-mannopyranose-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate 的选择性 3-O-糖基化获得的、6-O-二苯甲酰基-δ-d-吡喃甘露糖苷与 2,3,4,6-四-O-苯甲酰基-δ-d-吡喃甘露糖基-(1→2)-3,4,6-三-O-苯甲酰基-δ-d-吡喃甘露糖基-(1→2)-3,4,6-三-O-苯甲酰基-δ-d-吡喃甘露糖基三氯亚氨酸酯进行选择性 3-O-糖基化反应得到四糖。
• Synthesis of a mannose heptasaccharide of the pathogenic yeast, Candida glabrata IFO 0622 strain
  作者：Youlin Zeng、Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00162-3

  日期：2002.9

  An effective synthesis of the mannose heptasaccharide existing in the pathogenic yeast, Candida glabrata IFO 0622 strain was achieved via TMSOTf-promoted condensation of a tetrasaccharide donor 13 with a trisaccharide acceptor 16, followed by deprotection. The tetrasaccharide 13 was constructed by coupling of 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-mannopyranosyl trichloroacetimidate (7) with allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside (10), followed by deallylation and trichloroacetimadation. The trisaccharide 16 was obtained by coupling of 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate with 10, and subsequent 6-O-deacetylation. The disaccharide 7 was prepared through coupling of perbenzoylated mannosyl trichloroacetimidate with 4,6-O-benzylidene-1,2-O-ethylidene-beta-D-mannopyranose, then simultaneous debenzylidenation and deethylidenation, and subsequent acetylation, selective 1-O-deacetylation, and trichloroacetimidation. The disaccharide 10 was obtained by self-condensation of 3,4,6-tri-O-benzoyl-1,2-O-allyloxyethylidene-beta-D-mannopyranose, followed by selective 2-O-deacetylation. (C) 2002 Elsevier Science Ltd. All rights reserved.