(5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one | 193338-94-2

分子结构分类

有机化合物 - 苯类化合物 - 苯和取代衍生物

中文名称

——

中文别名

——

英文名称

(5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one

英文别名

3-carbethoxy-5(S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>dihydrofuran-2(3H)-one；5-(1-tert-butoxycarbonylamino-2-phenylethyl)-2-oxo-tetrahydrofuran-3-carboxylic avid ethyl ester；(4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-carbethoxydihydrofuran-2-2(3H)-one；(5S,1-S)-3-carboethoxy-5-(1-((1-,1-dimethylethoxycarbonyl)amino)-2-phenylethyl)-dihydrofuran-2-(3H)-one；(5S,1'S)-3-carboethoxy-5-(1-(Boc-amino)-2-phenylethyl)dihydrofuran-2(3H)-one；3-carbethoxy-5(S)-{1'-(S)-[(tert-butyloxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2(3H)-one；5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R,S)-ethoxycarbonyl-dihydrofuran-2-(3H)-one；ethyl (5S)-5-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]-2-oxooxolane-3-carboxylate

(5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one化学式

CAS

193338-94-2

化学式

C₂₀H₂₇NO₆

mdl

——

分子量

377.437

InChiKey

ALIRBAQAJOSDKA-YVZMLIKISA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

157.3 °C(Solv: heptane (142-82-5))
沸点：

543.8±45.0 °C(Predicted)
密度：

1.173±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

3.5
重原子数：

27
可旋转键数：

9
环数：

2.0
sp3杂化的碳原子比例：

0.55
拓扑面积：

90.9
氢给体数：

1
氢受体数：

6

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(R,S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>oxirane	220871-52-3	C₁₅H₂₁NO₃	263.337
(1S)-1-(2R)-环氧乙基-2-苯乙基氨基甲酸叔丁酯	(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane	98760-08-8	C₁₅H₂₁NO₃	263.337

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(3R,5S,1'S)-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>-3-methyldihydrofuran-2(3H)-one	104293-55-2	C₁₈H₂₅NO₄	319.401
——	(4S,5S)-5-<1-(t-Boc-amino)-2-phenylethyl>-3-(phenylmethyl)dihydrofuran-2(3H)-one	——	C₂₄H₂₉NO₄	395.499
——	(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one	98818-41-8	C₂₄H₂₉NO₄	395.499
——	{(S)-1-[(2S,4R)-4-(4-Methyl-benzyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester	155456-14-7	C₂₅H₃₁NO₄	409.525
——	(1S,2'S,4'R)-<1-<4'-(4''-fluorobenzyl)-5'-oxo-tetrahydrofuran-2'-yl>-2-phenylethyl>carbamic acid tert-butyl ester	150609-73-7	C₂₄H₂₈FNO₄	413.489
——	5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(4-biphenylyl)methyl]dihydrofuran-2-(3H)-one	178049-38-2	C₃₀H₃₃NO₄	471.596
——	(2R,4S,5S)-4-hydroxy-2-methyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhexanoic acid	154160-25-5	C₁₈H₂₇NO₅	337.416
——	5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid	98818-45-2	C₂₄H₃₁NO₅	413.514
——	(2R,4S,5S)-2-[(4-fluorophenyl)methyl]-4-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhexanoic acid	150609-74-8	C₂₄H₃₀FNO₅	431.504
——	5(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(4-biphenylyl)methyl]hexanoic acid	178049-39-3	C₃₀H₃₅NO₅	489.612
——	(2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic acid	123482-69-9	C₂₄H₄₁NO₅Si	451.679
——	N-(1,1-dimethylethoxycarbonyl)-5(S)-amino-4(S)-(t-butyldimethylsilyloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoic acid	98818-51-0	C₃₀H₄₅NO₅Si	527.777
——	(2R,4S,5S)-5-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-fluoro-benzyl)-6-phenyl-hexanoic acid	150609-75-9	C₃₀H₄₄FNO₅Si	545.767
——	(2R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenyl-2-[(4-phenylphenyl)methyl]hexanoic acid	178049-40-6	C₃₆H₄₉NO₅Si	603.874
——	(2R,4S,5S)-5-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-2-(4-trifluoromethyl-benzyl)-hexanoic acid	158654-80-9	C₃₁H₄₄F₃NO₅Si	595.775
N-{(2R,4S,5S)-2-苯甲基-5-[(叔-丁氧基羰基)氨基]-4-羟基-6-苯基己酰}-L-亮氨酰-L-苯丙氨酸酰胺	{(1S)-benzyl-(4R)-[1-((1S)-carbamoyl-2-phenyl-ethylcarbamoyl)-(1S)-3-methyl-butyl-carbamoyl]-(2S)-hydroxy-5-phenyl-pentyl} carbamic acid tert-butyl ester	126409-24-3	C₃₉H₅₂N₄O₆	672.865
——	tert-butyl N-[(2S,3S,5R)-5-{[(1S)-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-hydroxy-1-phenyl-5-[(4-phenylphenyl)methyl]pentan-2-yl]carbamate	——	C₄₅H₅₆N₄O₆	748.963
——	tert-butyl N-[(1S,2S,4R)-1-benzyl-2-hydroxy-4-[[(1S,2R)-2-hydroxyindan-1-yl]carbamoyl]nonadecyl]carbamate	——	C₄₁H₆₄N₂O₅	664.97
叔-丁基[(1S,2S,4R)-1,4-二苯甲基-2-羟基-5-{[(1S,2R)-2-羟基-2,3-二氢-1H-茚-1-基]氨基}-5-羰基戊基]氨基甲酸酯	L-685434	126456-36-8	C₃₃H₄₀N₂O₅	544.691
——	tert-butyl N-[(1S,2S,4R)-1-benzyl-2-hydroxy-4-[[4-(2-hydroxyethyl)phenyl]methyl]-5-[[(1S,2R)-2-hydroxyindan-1-yl]amino]-5-oxo-pentyl]carbamate	——	C₃₅H₄₄N₂O₆	588.744
——	tert-butyl N-[(1S,2S,4R)-1-benzyl-2-hydroxy-5-[[(1S,2R)-2-hydroxyindan-1-yl]amino]-4-[(4-iodophenyl)methyl]-5-oxo-pentyl]carbamate	——	C₃₃H₃₉IN₂O₅	670.588
——	N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-[1,1-dimethylethoxy-carbonylamino]-4(S)-hydroxy-6-phenyl-2(R)-(4-hydroxyphenylmethyl) hexanamide	138498-62-1	C₃₃H₄₀N₂O₆	560.69
——	[(1S,2S,4R)-1-Benzyl-2-hydroxy-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-(4-hydroxymethyl-phenyl)-pentyl]-carbamic acid tert-butyl ester	——	C₃₄H₄₂N₂O₆	574.717

反应信息

作为反应物：

描述：

(5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one 在咪唑、 lithium hydroxide 、四丁基氟化铵、 sodium ethanolate 、 1-羟基苯并三唑、盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺、三乙胺作用下，以四氢呋喃、乙二醇二甲醚、乙醇、 N,N-二甲基甲酰胺、甲苯为溶剂，反应 126.0h，生成 N-{(2R,4S,5S)-2-苯甲基-5-[(叔-丁氧基羰基)氨基]-4-羟基-6-苯基己酰}-L-亮氨酰-L-苯丙氨酸酰胺

参考文献：

名称：

HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: An investigation into the role of the P1' side chain on structure-activity

摘要：

A systematic investigation was undertaken to determine the role of the P1' sidechain in a series of hydroxyethylene isostere based inhibitors of HIV-1 protease. Substitution and homologation of the benzyl P1' side chain of the Phe-Phe isostere based pseudo peptides 1 (L-682,679) and 2 (L-685,434) with various heteroalkyl groups leads to a series of extremely potent inhibitors of the enzyme. Several examples of the most potent inhibitors were very effective in an ex vivo cell based viral spread assay using human H9 T-lymphocytes and the IIIb isolate of HIV-1. Compound 19 is 120 times more potent than 1 and 16 times more potent than 2 in inhibiting the spread of infection in this assay.

DOI：

10.1021/jm00088a004
作为产物：

描述：

(1S)-1-(2R)-环氧乙基-2-苯乙基氨基甲酸叔丁酯、