3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl bromide | 161545-20-6

分子结构分类

有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物

中文名称

——

中文别名

——

英文名称

3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl bromide

英文别名

[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-bromo-5-[(2,2,2-trichloroacetyl)amino]oxan-2-yl]methyl acetate

3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl bromide化学式

CAS

161545-20-6

化学式

C₁₄H₁₇BrCl₃NO₈

mdl

——

分子量

513.554

InChiKey

RXUXYXLYNAIOJC-OOCWMUITSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

1.9
重原子数：

27
可旋转键数：

8
环数：

1.0
sp3杂化的碳原子比例：

0.71
拓扑面积：

117
氢给体数：

1
氢受体数：

8

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetamido-D-glucopyranose	219693-02-4	C₁₆H₂₀Cl₃NO₁₀	492.695
——	ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamido)-1-thio-β-D-glucopyranoside	169557-88-4	C₁₆H₂₂Cl₃NO₈S	494.778

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	allyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside	1061181-49-4	C₁₇H₂₂Cl₃NO₉	490.722
——	[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-sulfanyl-5-[(2,2,2-trichloroacetyl)amino]oxan-2-yl]methyl acetate	219693-14-8	C₁₄H₁₈Cl₃NO₈S	466.724
——	2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside	702676-24-2	C₁₉H₃₀Cl₃NO₉Si	550.893
——	2-(trimethylsilyl)ethyl 2-deoxy-3,6-di-O-pivaloyl-2-trichloroacetamido-β-D-glucopyranoside	702676-28-6	C₂₃H₄₀Cl₃NO₈Si	593.017
——	allyl 4-O-acetyl-6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside	765910-46-1	C₂₅H₃₀Cl₃NO₉	594.874
——	3,4,6-tri-O-acetyl-2-N-trichloroacetyl-S-acetyl-1-thio-β-D-glucosamine	219693-13-7	C₁₆H₂₀Cl₃NO₉S	508.761
——	2-(trimethylsilyl)ethyl 2-deoxy-4,6-di-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside	702676-29-7	C₂₃H₄₀Cl₃NO₈Si	593.017
——	allyl 6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside	765910-31-4	C₂₃H₂₈Cl₃NO₈	552.836
——	allyl 4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside	765910-45-0	C₂₃H₂₆Cl₃NO₈	550.82
——	allyl 4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside	765910-32-5	C₂₀H₂₄Cl₃NO₇	496.772
——	allyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside	399036-13-6	C₇₁H₆₆Cl₃NO₂₅	1439.66
——	benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1<*>3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside	161545-24-0	C₄₈H₄₆Cl₃NO₁₇	1015.25
——	methyl 3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-18β-glycyrrhetinate	1173698-20-8	C₄₅H₆₄Cl₃NO₁₂	917.362
——	methyl 4)-2,3-di-O-benzyl-β-D-glucopyranosid>uronate	161545-35-3	C₃₆H₄₂Cl₃NO₁₅	835.086
——	phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl-(1→6)-1-thio-β-D-galactopyranoside	1439813-85-0	C₂₆H₃₂Cl₃NO₁₃S	704.964
——	phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside	1439813-54-3	C₂₆H₃₂Cl₃NO₁₃S	704.964
——	phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl-(1→6)-1-thio-α-D-mannopyranoside	1439814-08-0	C₂₆H₃₂Cl₃NO₁₃S	704.964
——	diphenylmethyl 3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-18β-glycyrrhetinate	1173698-21-9	C₅₇H₇₂Cl₃NO₁₂	1069.56
——	2-(trimethylsilyl)ethyl β-D-galactopyranosyl-(1->3)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside	702676-40-2	C₁₉H₃₄Cl₃NO₁₁Si	586.924
——	(2R,3S,4S,5R,6R)-2-((benzoyloxy)methyl)-6-(((2S,4aR,6R,7R,8R,8aR)-2-phenyl-7-(2,2,2-trichloroacetamido)-6-(2-(trimethylsilyl)ethoxy)hexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate	702676-38-8	C₅₄H₅₄Cl₃NO₁₅Si	1091.46
——	allyl O-(2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside	399036-29-4	C₆₈H₆₄Cl₃NO₂₂	1353.61
——	allyl 2-deoxy-2-trichloroacetamido-β-D-glucopyranoside	——	C₁₁H₁₆Cl₃NO₆	364.61
——	2-(trimethylsilyl)ethyl 2-deoxy-2-trichloroacetamido-β-D-glucopyranoside	702676-26-4	C₁₃H₂₄Cl₃NO₆Si	424.781
——	2-(trimethylsilyl)ethyl 2-deoxy-2-trichloroacetamido-β-D-galactopyranoside	702676-32-2	C₁₃H₂₄Cl₃NO₆Si	424.781
——	(2R,3R,4S,5S,6R)-2-(((2S,4aR,6R,7R,8R,8aR)-7-acetamido-2-phenyl-6-(2-(trimethylsilyl)ethoxy)hexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate	702676-42-4	C₅₄H₅₇NO₁₅Si	988.13
——	2-(trimethylsilyl)ethyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside	150571-26-9	C₁₉H₃₇NO₁₁Si	483.588

反应信息

作为反应物：

描述：

3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl bromide 在 2,4,6-三甲基吡啶、四丁基溴化铵作用下，以 1,2-二氯乙烷为溶剂，反应 0.5h，以92%的产率得到2-trichloromethyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)<2,1-d>2-oxazoline

参考文献：

名称：

2-脱氧-2-三氯乙酰氨基-d-吡喃葡萄糖衍生物在寡糖合成中的应用

摘要：

测试了3,4,6-三-O-乙酰基-2-脱氧-2-三氯乙酰氨基-α-D-吡喃葡糖基三氯乙酰亚氨酸酯及其O-苄基类似物与一组未在O上取代的糖受体在反应中的糖基供体-3和O-4，通常在寡糖合成中遇到。以良好至极好的收率获得糖苷，仅略微过量（1.1-1.2当量）的供体，并具有高度的1，2-反式立体选择性。假定相应的2-（三氯甲基）恶唑啉鎓离子是主要的反应性中间体。在中性条件下，通过用三丁基锡烷还原，二糖产物中的N-三氯乙酰基很容易转化为N-乙酰基。

DOI：

10.1016/0008-6215(94)84038-5
作为产物：

描述：

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose 在