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2,3,4-tri-O-benzoyl-6-O-benzyl-α-D-galactopyranosyl bromide | 175978-01-5

中文名称
——
中文别名
——
英文名称
2,3,4-tri-O-benzoyl-6-O-benzyl-α-D-galactopyranosyl bromide
英文别名
[(2R,3S,4S,5R,6R)-4,5-dibenzoyloxy-6-bromo-2-(phenylmethoxymethyl)oxan-3-yl] benzoate
2,3,4-tri-O-benzoyl-6-O-benzyl-α-D-galactopyranosyl bromide化学式
CAS
175978-01-5
化学式
C34H29BrO8
mdl
——
分子量
645.503
InChiKey
TWMOCBUFCAQROO-NBCLCUQJSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    7
  • 重原子数:
    43
  • 可旋转键数:
    13
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.21
  • 拓扑面积:
    97.4
  • 氢给体数:
    0
  • 氢受体数:
    8

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Preparative route to N-glycolylneuraminic acid phenyl 2-thioglycoside donor and synthesis of Neu5Gc-α-(2→3′)-lactosamine 3-aminopropyl glycoside
    摘要:
    The spacer-armed trisaccharide, Neu5Ge-alpha-(2-->3')-lactosamine 3-aminopropyl glycoside, was synthesized by regio- and stereoselective sialylation of the suitably protected triol acceptor. 3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(6-O-benzyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside, with the donor methyl [phenyl 5-acetoxyacetamido-4.7,8.9-tetra-O-acetyl-3.5-dideoxy-2-thio-D-glycero-alpha,beta-D-galacto-2-nonulopyranosid]onate. The donor was obtained. in turn, from methyl [phenyl 5-acetamido-4,7,8.9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-alpha,beta-D-galacto-2-nonulopyranosid]onate by N-tert-butoxycarbonylation of the acetamido group followed by total N- and O-deacetylation, per-O-acetylation, subsequent Boc group removal, and N-acetoxyacetylation. (C) 2002 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0008-6215(02)00003-4
  • 作为产物:
    描述:
    苯基-1-硫醇-beta-D-半乳糖苷吡啶盐酸calcium sulfate乙醚 、 3 A molecular sieve 、 四乙基溴化铵 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下, 以 二氯甲烷N,N-二甲基甲酰胺 为溶剂, 反应 28.08h, 生成 2,3,4-tri-O-benzoyl-6-O-benzyl-α-D-galactopyranosyl bromide
    参考文献:
    名称:
    从人类慢性粒细胞白血病细胞中分离出的VIM-2神经节苷脂的全合成
    摘要:
    描述了肿瘤相关糖脂抗原VIM-2的全合成[2]。苯基2,3,4-三-O-苯甲酰基-6-O-苄基-β-D-吡喃半乳糖基-(1-> 4)-6-O-苄基l-2-脱氧-2-邻苯二甲酰亚胺-1-硫代β-D-吡喃葡萄糖苷(7)是通过将苯基6-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代β-D-吡喃葡萄糖苷(6)与2,3缩合制得的关键中间体,将4-三-O-苯甲酰基-6-O-苄基-α-D-吡喃半乳糖基溴化物(5)与甲基2,3,4-三-O-苄基-1-硫代-β-L-呋喃二糖苷( 8)得到三糖供体9,其与2-(三甲基甲硅烷基)乙基2,4,6-三-O-苄基-β-D-吡喃半乳糖基-(1→4)-2,3偶联, 6-三-O-苄基是ta-D-吡喃葡萄糖苷(10),得到五糖11。12的区域选择性糖基化(通过11的O-去苯甲酰化获得)得到七糖13,
    DOI:
    10.1016/0008-6215(95)00353-3
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文献信息

  • Total synthesis of VIM-2 ganglioside isolated from human chronic myelogenous leukemia cells
    作者:Taro Ehara、Akihiko Kameyama、Yutaka Yamada、Hideharu Ishida、Makoto Kiso、Akira Hasegawa
    DOI:10.1016/0008-6215(95)00353-3
    日期:1996.2
    A total synthesis of the tumor-associated glycolipid antigen, VIM-2, is described [2]. Phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-beta-D-galactopyranosyl-(1-->4)-6-O-benzy l-2- deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (7), a key intermediate prepared by condensation of phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (6) and 2,3,4-tri-O-benzoyl-6-O-benzyl-alpha-D-galactopyranosyl
    描述了肿瘤相关糖脂抗原VIM-2的全合成[2]。苯基2,3,4-三-O-苯甲酰基-6-O-苄基-β-D-吡喃半乳糖基-(1-> 4)-6-O-苄基l-2-脱氧-2-邻苯二甲酰亚胺-1-硫代β-D-吡喃葡萄糖苷(7)是通过将苯基6-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代β-D-吡喃葡萄糖苷(6)与2,3缩合制得的关键中间体,将4-三-O-苯甲酰基-6-O-苄基-α-D-吡喃半乳糖基溴化物(5)与甲基2,3,4-三-O-苄基-1-硫代-β-L-呋喃二糖苷( 8)得到三糖供体9,其与2-(三甲基甲硅烷基)乙基2,4,6-三-O-苄基-β-D-吡喃半乳糖基-(1→4)-2,3偶联, 6-三-O-苄基是ta-D-吡喃葡萄糖苷(10),得到五糖11。12的区域选择性糖基化(通过11的O-去苯甲酰化获得)得到七糖13,
  • Preparative route to N-glycolylneuraminic acid phenyl 2-thioglycoside donor and synthesis of Neu5Gc-α-(2→3′)-lactosamine 3-aminopropyl glycoside
    作者:Andrei A. Sherman、Olga N. Yudina、Alexander S. Shashkov、Vladimir M. Menshov、Nikolay E. Nifantiev
    DOI:10.1016/s0008-6215(02)00003-4
    日期:2002.3
    The spacer-armed trisaccharide, Neu5Ge-alpha-(2-->3')-lactosamine 3-aminopropyl glycoside, was synthesized by regio- and stereoselective sialylation of the suitably protected triol acceptor. 3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(6-O-benzyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside, with the donor methyl [phenyl 5-acetoxyacetamido-4.7,8.9-tetra-O-acetyl-3.5-dideoxy-2-thio-D-glycero-alpha,beta-D-galacto-2-nonulopyranosid]onate. The donor was obtained. in turn, from methyl [phenyl 5-acetamido-4,7,8.9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-alpha,beta-D-galacto-2-nonulopyranosid]onate by N-tert-butoxycarbonylation of the acetamido group followed by total N- and O-deacetylation, per-O-acetylation, subsequent Boc group removal, and N-acetoxyacetylation. (C) 2002 Elsevier Science Ltd. All rights reserved.
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