3,6-di-O-allyl-2,4-di-O-benzyl-D-mannopyranose | 89067-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-di-O-allyl-2,4-di-O-benzyl-D-mannopyranose
• 英文别名: (3S,4S,5R,6R)-3,5-bis(phenylmethoxy)-4-prop-2-enoxy-6-(prop-2-enoxymethyl)oxan-2-ol
• CAS: 89067-94-7
• 化学式: C₂₆H₃₂O₆
• 分子量: 440.536
• InChiKey: DLCWNPOQLCIWRZ-APQRZRNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-di-O-allyl-2,4-di-O-benzyl-D-mannopyranose 生成 3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl p-nitrobenzoate
  参考文献：
  名称：

  YAMAZAKI, FUMITO;KITAJIMA, TOHRU;NUKADA, TOMOO;ITO, YUKISHIGE;OGAWA, TOMO+, CARBOHYDR. RES. , 201,(1990) N, C. 15-30

  摘要：

  DOI：
• 作为产物：
  描述：

  3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl acetate 在 水 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.0h， 以85%的产率得到3,6-di-O-allyl-2,4-di-O-benzyl-D-mannopyranose
  参考文献：
  名称：

  Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of “bisected” complex-type glycans of a glycoprotein

  摘要：

  A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(90)84222-g

文献信息

• Efficient and Concise Synthesis of βMan1–4GlcN Linkage of Pentasaccharide Core by Using 6-Nitro-2-benzothiazolyl α-Mannoside
  作者：Hiroki Mandai、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.702

  日期：2005.5

  Efficient and concise synthesis of βMan1–4GlcN of pentasaccharide core is established; direct β-mannosylations of 4-OH group of 2-deoxy-2-phthaloyl and 2-azide-2-deoxy glucose derivatives by using 6-nitro-2-benzothiazolyl α-mannoside proceeded smoothly to afford the desired β-mannosides in high yields.

  利用 6-硝基-2-苯并噻唑基 α-甘露糖苷对 2-脱氧-2-邻苯二甲酰和 2-叠氮-2-脱氧葡萄糖衍生物的 4-OH基团进行直接 β-甘露糖苷化，顺利合成了五糖核心的 βMan1-4GlcN ，并获得了高产率的所需 β-甘露糖苷。
• 6-Nitro-2-benzothiazolyl α-Mannoside: A Highly Efficient Mannosyl Donor in Constructing β-Man(1→4)GlcN Linkage and Its Application to the Synthesis of the Pentasaccharide Core of<i>N</i>-Glycans
  作者：Hiroki Mandai、Teruaki Mukaiyama

  DOI：10.1246/bcsj.79.479

  日期：2006.3

  An efficient and concise synthesis of the β-Man(1→4)GlcN linkage that exists in N-linked glycans has been established. Direct β-mannosylations of the 4-OH group of glucosamine derivatives by using ...

  已经建立了存在于 N-连接聚糖中的 β-Man(1→4)GlcN 键的高效简明合成。葡萄糖胺衍生物的 4-OH 基团的直接 β-甘露糖基化...
• YAMAZAKI, FUMITO;KITAJIMA, TOHRU;NUKADA, TOMOO;ITO, YUKISHIGE;OGAWA, TOMO+, CARBOHYDR. RES. , 201,(1990) N, C. 15-30
  作者：YAMAZAKI, FUMITO、KITAJIMA, TOHRU、NUKADA, TOMOO、ITO, YUKISHIGE、OGAWA, TOMO+

  DOI：——

  日期：——
• Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of “bisected” complex-type glycans of a glycoprotein
  作者：Fumito Yamazaki、Tohru Kitajima、Tomoo Nukada、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/0008-6215(90)84222-g

  日期：1990.6

  A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.