N-(benzyloxycarbonyl)-[2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-(1->3)-α-D-galactopyranosyl]-L-serine | 114117-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(benzyloxycarbonyl)-[2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-(1->3)-α-D-galactopyranosyl]-L-serine
• CAS: 114117-02-1
• 化学式: C₂₅H₃₆N₂O₁₅
• 分子量: 604.565
• InChiKey: NWCVRZNOADFSGY-KRAOEAFBSA-N

物化性质

• 沸点：
  973.8±65.0 °C(predicted)
• 密度：
  1.56±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.85
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  263.03
• 氢给体数：
  9.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-[2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-(1->3)-α-D-galactopyranosyl]-L-serine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 T表位,丝氨酰
  参考文献：
  名称：

  Cyclic di-t-butylsilylenediyl ether group as a convenient protective group for the glycoconjugate synthesis

  摘要：

  Treatment of methyl B-D-glucopyranoside, methyl alpha -D-glucopyranoside, 2-azido-2-deoxy-beta -D-galactopyranosyl fluoride, and 1,6-anhydro-beta -lactose with di-t-butyldichlorosilane gave the corresponding 4.6-cyclic di-t-butylsilylenediyl ether (4,6-CDBS) derivatives in high yields. It was suggested that the 4,6-CDBS group is quite stable under general conditions for further chemical manipulations such as the acetylation, benzylation and glycosylation reactions employed widely in the carbohydrate chemistry. This protective group was readily removed by treatment with tetrabutylammonium fluoride or triethylamine-3HF complex under mild conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00044-2
• 作为产物：
  描述：

  (4aR,6S,7R,8R,8aR)-7-azido-2,2-ditert-butyl-6-fluoro-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-ol 在 吡啶 、 sodium hydroxide 、 二氯二茂锆 、 三氟甲磺酸三甲基硅酯 、 silver perchlorate 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 25.33h， 生成 N-(benzyloxycarbonyl)-[2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-(1->3)-α-D-galactopyranosyl]-L-serine
  参考文献：
  名称：

  Cyclic di-t-butylsilylenediyl ether group as a convenient protective group for the glycoconjugate synthesis

  摘要：

  Treatment of methyl B-D-glucopyranoside, methyl alpha -D-glucopyranoside, 2-azido-2-deoxy-beta -D-galactopyranosyl fluoride, and 1,6-anhydro-beta -lactose with di-t-butyldichlorosilane gave the corresponding 4.6-cyclic di-t-butylsilylenediyl ether (4,6-CDBS) derivatives in high yields. It was suggested that the 4,6-CDBS group is quite stable under general conditions for further chemical manipulations such as the acetylation, benzylation and glycosylation reactions employed widely in the carbohydrate chemistry. This protective group was readily removed by treatment with tetrabutylammonium fluoride or triethylamine-3HF complex under mild conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00044-2

文献信息

• Chemo-enzymatic synthesis of C-9 acetylated sialosides
  作者：Jana Rauvolfova、Andre Venot、Geert-Jan Boons

  DOI：10.1016/j.carres.2008.05.002

  日期：2008.7

  Abstract A chemo-enzymatic synthesis of [(5-acetamido-9-O-acetyl-3,5-dideoxy-d-glycero-α-d-galacto-2-nonulopyranosylonic acid)-(2→3)-O-(β-d-galactopyranosyl)-(1→3)-O-(2-acetamido-2-deoxy-α-d-galactopyranosyl)]-l-serine acetate (1) has been accomplished by a regioselective chemical acetylation of Neu5Ac (2) to give 9-O-acetylated sialic acid 3, which was enzymatically converted into CMP-Neu5,9Ac2 (4)

  摘要化学合成[[5-乙酰氨基-9-O-乙酰基-3,5-二脱氧-d-甘油-α-d-半乳糖-2-壬基吡咯烷酸]-（2→3）-O-（ β-d-吡喃半乳糖基）-（1→3）-O-（2-乙酰氨基-2-脱氧-α-d-吡喃半乳糖基）]-1-丝氨酸乙酸酯（1）已通过Neu5Ac（ 2）得到9-O-乙酰化的唾液酸3，使用来自脑膜炎奈瑟氏菌的重组CMP-唾液酸合成酶将其酶促转化为CMP-Neu5,9Ac2（4）[EC 2.7.7.43]。然后使用在鼠尾夜蛾（Spodooptera frugiperda）中表达的重组大鼠α-（2→3）-O-唾液酸转移酶将所得化合物用于化学制备的糖基化氨基酸10的C-3'羟基的酶糖基化反应[EC 2.4.99.4]丝氨酸的Nα-苄氧基羰基（CBz）保护基脱保护后，目标化合物1。