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(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol | 284490-14-8

分子结构分类

有机化合物 - 有机杂环化合物 - 吡咯烷类

中文名称

——

中文别名

——

英文名称

(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

英文别名

1,1-Dimethylethyl (3aS,4S,6R,6aR)-4-[(1Z)-1-cyano-2-hydroxyethenyl]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5H-1,3-dioxolo[4,5-c]pyrrole-5-carboxylate；tert-butyl (3aS,4S,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[(Z)-1-cyano-2-hydroxyethenyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol化学式

CAS

284490-14-8

化学式

C₂₂H₃₈N₂O₆Si

mdl

——

分子量

454.639

InChiKey

JXRVZIDPWUDVAH-XHCSWFMASA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

543.6±50.0 °C(Predicted)
密度：

1.085±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

4.48
重原子数：

31
可旋转键数：

7
环数：

2.0
sp3杂化的碳原子比例：

0.82
拓扑面积：

101
氢给体数：

1
氢受体数：

7

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
2-[2-[[5-亚氨基-3-甲基-1-(8-磺酸根-2-萘基)-4H-吡唑-4-基]偶氮]-5-[4-[[5-亚氨基-3-甲基-1-(8-磺酸根-2-萘基)-4H-吡唑-4-基]偶氮]-3-(2-羟基-2-羰基-乙氧基)苯基]苯氧基]乙酸四钠	N-tert-butoxycarbonyl-7-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3,6-imino-4,5-O-isopropylidene-D-allo-heptononitrile	222631-09-6	C₂₁H₃₈N₂O₅Si	426.629
1H-咪唑并[1,2-b]吡唑-2-醇,7-氨基-6-甲基-	7-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3,6-imino-4,5-O-isopropylidene-D-allo-heptononitrile	222631-08-5	C₁₆H₃₀N₂O₃Si	326.511
(3AR,4R,6AS)-4-[[[(叔丁酯)二甲基硅烷基]氧基]甲基]四氢-2,2-二甲基-4H-1,3-二氧杂环戊烯并[4,5-C]吡咯	5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	153172-31-7	C₁₄H₂₉NO₃Si	287.475

下游产品

中文名称	英文名称	CAS号	化学式	分子量
2-氯-N-(2,3-二甲基苯基)-N-(丙烷-2-基)乙酰胺	(3aR,4R,6S,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(Z)-1-cyano-2-(cyanomethyl-amino)-vinyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester	222631-45-0	C₂₄H₄₀N₄O₅Si	492.691
噻吩并[2,3-b]吡啶,2,3-二氢-6-甲基-4-苯基-	N-tert-butoxycarbonyl-7-O-tert-butyldimethylsilyl-2-cyano-1,2,3,6-tetradeoxy-1-N-(ethoxycarbonylmethylamino)-3,6-imino-4,5-O-isopropylidene-D-allo-hept-1-enitol	222631-11-0	C₂₆H₄₅N₃O₇Si	539.745
1H-环丙烯并[3,4]环戊二烯并[1,2-d]咪唑(9CI)	tert-butyl (3aS,4S,6R,6aR)-4-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate	222631-47-2	C₂₅H₄₁N₅O₅Si	519.717
——	(3aS,4S,6R,6aR)-tert-butyl 4-(4-amino-5-(ethoxycarbonyl)-1H-pyrrol-3-yl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate	284490-15-9	C₂₆H₄₅N₃O₇Si	539.745
2(3H)-噻唑亚胺,3-乙基-4-甲基-	(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-(9-deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	222631-13-2	C₂₅H₄₀N₄O₆Si	520.701
2-乙酰氨基-2-脱氧-D-半乳酸*1,4-内酯	(1S)-1-C-(3-amino-1-N-benzyloxycarbonyl-2-cyano-4-pyrrolyl)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	222631-46-1	C₃₂H₄₆N₄O₇Si	626.825
b-D-半乳吡喃糖,1,6-脱水-,3-乙酸酯2-[二(苯基甲基)磷酸酯](9CI)	(1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	222631-12-1	C₃₄H₅₁N₃O₉Si	673.879
噁丙环,甲基-,聚合噁丙环,单辛基醚,磷酸酯	(1S)-1-[3-(N-benzoyl-S-methylisothiocarbamoyl)imino-2-ethoxycarbonylpyrrol-4-yl]-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	222631-14-3	C₃₅H₅₂N₄O₈SSi	716.971
——	(1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	284490-17-1	C₂₈H₃₇N₃O₉	559.616
——	(1S)-1-(9-deazaguanidin-9-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	284490-16-0	C₁₉H₂₇N₅O₆	421.453
[(3E)-6-羰基-3-{2-[4-(吡啶-2-基氨磺酰)苯基]肼亚基}环己-1,4-二烯-1-基]乙酸	(1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-5-bromo-N-tert-butoxycarbonyl-1,4,5-trideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	222631-38-1	C₂₈H₃₆BrN₃O₈	622.513
磷酸氢[(2R,3R,4R,5R)-4-[[(2R,3S,4R,5R)-3,4-二羟基-5-(6-硫代-3H-嘌呤-9-基)四氢呋喃-2-基]甲氧基]-3-羟基-5-(6-硫代-3H-嘌呤-9-基)四氢呋喃-2-基]甲酯磷羧酯	1(S)-1-C-[3-(1-benzamido-1-methylthio-methyleneamino)-2-ethoxycarbonyl-4-pyrrolyl]-N-tert-butoxycarbonyl-1,4,5-trideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol	222631-42-7	C₂₉H₃₈N₄O₇S	586.709
1-苯并噁庚-5(2H)-酮,7-乙基-3,4-二氢-3-(甲基氨基)-	tert-butyl (3aS,4S,6R,6aR)-4-(2-amino-4-oxo-3,5-dihydropyrrolo[3,2-d]pyrimidin-7-yl)-2,2,6-trimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate	222631-43-8	C₁₉H₂₇N₅O₅	405.454
5H-环戊二烯并[e]吡啶并[1,2-c][1,3]噁嗪,十氢-7-甲基-,(3aa,7b,10aa,10bb)-(9CI)	tert-butyl (3aS,4S,6R,6aR)-4-(4-amino-5-ethoxycarbonyl-1H-pyrrol-3-yl)-2,2,6-trimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate	222631-39-2	C₂₀H₃₁N₃O₆	409.483
(2E)-6-氨基-4-(1,4'-联哌啶-1'-基)-2-亚氨基嘧啶-1(2H)-酚二盐酸	tert-butyl (3aS,4S,6R,6aR)-2,2,6-trimethyl-4-(4-oxo-3,5-dihydropyrrolo[3,2-d]pyrimidin-7-yl)-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate	222631-40-5	C₁₉H₂₆N₄O₅	390.439

反应信息

作为反应物：

描述：

(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol 在 palladium on activated charcoal 氢气、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯、三氟乙酸作用下，以甲醇、乙醇、二氯甲烷为溶剂，反应 39.0h，生成 7-[(2S,3S,4R,5R)-3,4-二羟基-5-(羟甲基)-2-吡咯烷基]-3,5-二氢-4H-吡咯并[3,2-D]嘧啶-4-酮

参考文献：

名称：

Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases

摘要：

Syntheses of the 'Immucillins', potent aza-C-nncleoside inhibitors of purine nucleoside phosphorylase are reported as well as those of 5-deoxy-, 5-deoxyfluoro- and 2-deoxy- analogues and others having modified bases. (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI：

10.1016/s0040-4020(00)00194-0
作为产物：

描述：

2-[2-[[5-亚氨基-3-甲基-1-(8-磺酸根-2-萘基)-4H-吡唑-4-基]偶氮]-5-[4-[[5-亚氨基-3-甲基-1-(8-磺酸根-2-萘基)-4H-吡唑-4-基]偶氮]-3-(2-羟基-2-羰基-乙氧基)苯基]苯氧基]乙酸四钠在溶剂黄146 作用下，以四氢呋喃、 N,N-二甲基甲酰胺为溶剂，反应 2.5h，生成 (1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

参考文献：

名称：

Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases

摘要：

Syntheses of the 'Immucillins', potent aza-C-nncleoside inhibitors of purine nucleoside phosphorylase are reported as well as those of 5-deoxy-, 5-deoxyfluoro- and 2-deoxy- analogues and others having modified bases. (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI：

10.1016/s0040-4020(00)00194-0

点击查看最新优质反应信息

文献信息

Transition-State Interactions Revealed in Purine Nucleoside Phosphorylase by Binding Isotope Effects

作者：Andrew S. Murkin、Peter C. Tyler、Vern L. Schramm

DOI：10.1021/ja7104398

日期：2008.2.1

The binding of [5‘-3H]inosine to human purine nucleoside phosphorylase results in an equilibrium binding isotope effect (BIE) of 1.5%, and transition state formation causes an intrinsic KIE of 4.7%. These values reflect atomic vibrational distortions in the 5‘-C−H bonds upon formation of the Michaelis complex and transition state. The degree of atomic distortion for catalysis is compared to that for

[5'-3H] 肌苷与人嘌呤核苷磷酸化酶的结合导致 1.5% 的平衡结合同位素效应 (BIE)，过渡态形成导致 4.7% 的内在 KIE。这些值反映了 Michaelis 配合物和过渡态形成后 5'-C-H 键中的原子振动畸变。将催化的原子畸变程度与过渡态类似物的结合程度进行比较。过渡态类似物 ImmH 和 DADMe-ImmH 的类似放射性标记形式分别产生 12.6% 和 29.2% 的大 5'-3H BIE。与过渡态类似物形成复合物时发生更大的键扭曲，在过渡态支持比与过渡态类似物形成复合物时更弱的扭曲力。
Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases

作者：Gary B. Evans、Richard H. Furneaux、Graeme J. Gainsford、Vern L. Schramm、Peter C. Tyler

DOI：10.1016/s0040-4020(00)00194-0

日期：2000.5

Syntheses of the 'Immucillins', potent aza-C-nncleoside inhibitors of purine nucleoside phosphorylase are reported as well as those of 5-deoxy-, 5-deoxyfluoro- and 2-deoxy- analogues and others having modified bases. (C) 2000 Elsevier Science Ltd. All rights reserved.