tert-butyldiphenylsilyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid-(2->3)-2,6-di-O-benzyl-D-galactopyranosyl-(1->4)-2-azido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranosisde-(1b->4a)-lactone | 227286-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldiphenylsilyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid-(2->3)-2,6-di-O-benzyl-D-galactopyranosyl-(1->4)-2-azido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranosisde-(1b->4a)-lactone
• CAS: 227286-38-6
• 化学式: C₉₅H₁₀₂N₄O₁₇Si
• 分子量: 1599.96
• InChiKey: ONYXGFUYUFIXPB-FNNQGONBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.95
• 重原子数：
  117.0
• 可旋转键数：
  37.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  233.38
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  tert-butyldiphenylsilyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid-(2->3)-2,6-di-O-benzyl-D-galactopyranosyl-(1->4)-2-azido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranosisde-(1b->4a)-lactone 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 N-[(2S,2'R,3'R,4'S,4aS,5R,7S,8R,8aS)-7-[(2R,3S,4R,5R)-5-azido-6-hydroxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3-oxo-4',8-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-2'-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,6'-oxane]-3'-yl]acetamide 、 N-[(2S,2'R,3'R,4'S,4aS,5R,7R,8R,8aS)-7-[(2R,3S,4R,5R)-5-azido-6-hydroxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3-oxo-4',8-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-2'-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,6'-oxane]-3'-yl]acetamide
  参考文献：
  名称：

  The first total synthesis of the core class II disialylated hexasaccharide as a building block for glycopeptide synthesis

  摘要：

  The first total synthesis of the protected core class II sialylated glycosyl-Thr hexasaccharide (3), utilizing suitably protected building blocks 4, 5, 7 and 8 was accomplished. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00605-x
• 作为产物：
  描述：

  5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid-(2->3)-2,6-di-O-benzyl-α,β-D-galactopyranosyl trichloroacetimidate-(1b->4a)-lactone 、 t-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-dlucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以75%的产率得到tert-butyldiphenylsilyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid-(2->3)-2,6-di-O-benzyl-D-galactopyranosyl-(1->4)-2-azido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranosisde-(1b->4a)-lactone
  参考文献：
  名称：

  An efficient access to protected disialylated glycohexaosyl threonine present on the leukosialin of activated T-lymphocytes

  摘要：

  The total synthesis of the threonine-linked core 2 class disialylated hexasaccharide in a completely protected form was accomplished for the first time. The L-threonine conjugate, N-(9-fluorenylmethoxycarbonyl)-O-{(5-acetomido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylanic acid)-(2 --> 3)-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1 --> 4)-2-acetamido-2-deoxy-3,6-di-O-benzyl-beta-D-glucopyranosyl-(1 --> 6)-[(5-acctamido-4,7,8,9-tetra-O-benzyl-3, 5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2 --> 3)-2,6-di-O-benzyl-beta-D-galactopyranosyl-(1 --> 3)]-2-acetamido-2-deoxy-alpha-D-galactopyranosyl-(1d --> 4c:1f --> 4e)-dilactone}-L-threonine allyl ester was synthesized via stereocontrolled glycosylations employing readily accessible monosaccharidic blocks; t-butyl-diphenylsilyl-2-azido-2-deoxy-3, 6-di-O-benzyl-beta-D-glucopyranose, N-(9-fluorenylmethoxycarbonyl)-O-(2-azir-butylditnethylsilyl-2-deoxy-alpha-D-galactopyranosyl)-L-threonine allyl ester, 8, 9 and N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-alpha-D-galactopyranosy;)-L-threonine allyl ester. For the introduction of the amino acid. the azide group was used to temporarily mask the amino group of GalNAc so as to obtain an alpha-glycosidic linkage without participation from the C-2 substituent. The threonine was attached to the sugar unit at the monosaccharide stage to avoid loss of oligosaccharide at a later stage. The Fmoc and allyl ester protected amino acid at the reducing end facilitates efficient glycopeptide synthesis on solid-phase support. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00313-4