5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nanulopyranosylonic acid-(2->3)-2,6-di-O-benzyl-α-D-galactopyranosyl-trichloroacetamidate (1b->4a)-lactone | 197630-86-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nanulopyranosylonic acid-(2->3)-2,6-di-O-benzyl-α-D-galactopyranosyl-trichloroacetamidate (1b->4a)-lactone
• 英文别名: [(2S,4'S,4aS,5R,5'R,6'R,7R,8R,8aS)-5'-acetamido-3-oxo-4',8-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-6'-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-7-yl] 2,2,2-trichloroethanimidate
• CAS: 197630-86-7
• 化学式: C₆₁H₆₃Cl₃N₂O₁₃
• 分子量: 1138.54
• InChiKey: BYSOTJKIWNHLRN-JZZIOKKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  79
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nanulopyranosylonic acid-(2->3)-2,6-di-O-benzyl-α-D-galactopyranosyl-trichloroacetamidate (1b->4a)-lactone 、 N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-6-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以54%的产率得到prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-4-[(2S,4'S,4aS,5R,5'R,6'R,7R,8R,8aS)-5'-acetamido-3-oxo-4',8-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-6'-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-7-yl]oxy-3-azido-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-hydroxyoxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
  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：

  三氯乙腈 、 生成 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nanulopyranosylonic acid-(2->3)-2,6-di-O-benzyl-α-D-galactopyranosyl-trichloroacetamidate (1b->4a)-lactone
  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

文献信息

• Solid-phase synthesis of the B-chain of human α2HS glycoprotein
  作者：Yoshiaki Nakahara、Yuko Nakahara、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0008-6215(98)00142-6

  日期：1998.7

  The B-chain of human alpha 2HS glycoprotein 1, a heptacosapeptide carrying a trisaccharide (sialyl T) side chain, was synthesized. Prior to the Fmoc-based solid-phase synthesis of the glycopeptide, the benzyl-protected glycosyl serine building block 6 was prepared via beta-stereoselective glycosylation of the 2-azido-2-deoxygalactosyl serine 11 with the sialyl galactosyl trichloroacetimidate 9. An automated peptide synthesizer was efficiently used for the elongation of the entire peptide chain except for the coupling with 6. The synthesized glycopeptide was cleaved from the resin by the TFA method. The resultant mixture of the benzylated glycopeptides was treated with TMSOTf-thioanisole in TFA and then with aq NaHCO3 and 1,4-dithiothreitol to give 1. (C) 1998 Elsevier Science Ltd. All rights reserved.