5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose | 96690-02-7

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

英文别名

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-α,β-D-ribofuranose；(3aR,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol；6-(((tert-butyldiphenylsilanyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol；2,3-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-D-ribofuranose；(3aR,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose化学式

CAS

96690-02-7

化学式

C₂₄H₃₂O₅Si

mdl

——

分子量

428.601

InChiKey

OOVHEXLXHQNNLL-NJTYFVPYSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

497.5±45.0 °C(Predicted)
密度：

1.16±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

2.8
重原子数：

30
可旋转键数：

6
环数：

4.0
sp3杂化的碳原子比例：

0.5
拓扑面积：

57.2
氢给体数：

1
氢受体数：

5

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	2,5-anhydro-6-O-[tert-butyl(diphenyl)silyl]-3,4-O-isopropylidene-D-altritol	476311-58-7	C₂₅H₃₄O₅Si	442.627
——	5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-D-ribitol	130222-85-4	C₂₄H₃₄O₅Si	430.616
——	2-((3aS,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)acetonitrile	1370007-62-7	C₂₆H₃₃NO₄Si	451.638
——	5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate	478367-12-3	C₂₆H₃₂Cl₃NO₅Si	572.988
——	(1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol	681853-93-0	C₂₅H₃₄O₄Si	426.628
——	5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone	130222-84-3	C₂₄H₃₀O₅Si	426.585
——	(((3aR,4R,6R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(tert-butyl)diphenylsilane	——	C₂₄H₃₁BrO₄Si	491.497
——	(R)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5S)-5-(2-methoxyvinyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol	1228689-08-4	C₂₆H₃₆O₅Si	456.654
——	1-{(4S,5R)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-trimethylsilanyl-propynol	212686-86-7	C₂₉H₄₂O₅Si₂	526.82
——	methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside	652991-32-7	C₅₄H₆₆O₁₀Si	903.198
——	5-(tert-butyldiphenylsilyl)-1-deoxy-1-hydroxyamino-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranose	557794-46-4	C₂₄H₃₃NO₅Si	443.615
——	2-[(3aR,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-bromoacetaldehyde	254114-36-8	C₂₆H₃₃BrO₅Si	533.535
——	2-((3aS,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-3-hydroxyacrylonitrile	——	C₂₇H₃₃NO₅Si	479.648
——	1-[(tert-butyldiphenylsilyl)oxy]-2-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]but-3-en-2-ol	902799-70-6	C₂₇H₃₆O₄Si	452.666
——	(1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol	952418-10-9	C₂₇H₃₆O₄Si	452.666
——	2-((3aS,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-3-(cyanomethoxy)acrylonitrile	——	C₂₉H₃₄N₂O₅Si	518.685
——	2-((3aS,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-3-(dimethylamino)acrylonitrile	1370007-65-0	C₂₉H₃₈N₂O₄Si	506.717
——	ethyl 2-[(3aR,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-bromoacetate	254114-37-9	C₂₈H₃₇BrO₆Si	577.588
——	2-((3aS,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-3-(cyanomethylamino)acrylonitrile	1370008-42-6	C₂₉H₃₅N₃O₄Si	517.7
——	2-(2-((3aS,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-cyanovinyl)hydrazinecarbothioamide	1370008-19-7	C₂₈H₃₆N₄O₄SSi	552.77
——	2-((3aS,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-cyanovinyl methanesulfonate	1370007-67-2	C₂₈H₃₅NO₇SSi	557.74
——	tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane	177471-62-4	C₃₀H₃₆O₄Si	488.699
——	methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1,3-dideoxy-D-ribo-hept-2-enitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside	652991-31-6	C₅₄H₆₄O₉Si	885.182
——	3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1H-pyrrole	637009-14-4	C₂₈H₃₅NO₄Si	477.676
——	3-[(3aS,4R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1H-pyrrole	637009-15-5	C₂₈H₃₅NO₄Si	477.676
——	3-[(3aS,4S,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrrole-2,5-dione	170897-53-7	C₂₈H₃₃NO₆Si	507.659
——	3-[(3aS,4R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione	637009-16-6	C₂₈H₃₃NO₆Si	507.659
(3Ar,6ar)-6-((叔丁基二苯基甲硅烷基氧基)甲基)-2,2-二甲基-3ah-环戊并[d][1,3]二氧代l-4(6ah)-酮	(3aR,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one	303963-92-0	C₂₅H₃₀O₄Si	422.596
——	[3-[(3aS,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrrol-1-yl]-tri(propan-2-yl)silane	637009-12-2	C₃₇H₅₅NO₄Si₂	634.019
——	[3-[(3aS,4S,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrrol-1-yl]-tri(propan-2-yl)silane	637009-13-3	C₃₇H₅₅NO₄Si₂	634.019
——	4-[(3aS,4S,6R,6aR)-6-[(tert-butyl(diphenyl)silyl)oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-amino-thiophene-2-carbonitrile	1370007-66-1	C₂₉H₃₄N₂O₄SSi	534.751
——	3-amino-4-((3aS,4S,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)furan-2-carbonitrile	1370008-06-2	C₂₉H₃₄N₂O₅Si	518.685
——	3-amino-4-((3aS,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1H-pyrrole-2-carbonitrile	1370008-43-7	C₂₉H₃₅N₃O₄Si	517.7
——	(4-((3aS,4S,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-cyanothiophen-3-yl)-N,N-dimethylformimidamide	1370007-72-9	C₃₂H₃₉N₃O₄SSi	589.831
——	(4-((3aS,4S,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-cyanofuran-3-yl)-N,N-dimethylformimidamide	1370008-15-3	C₃₂H₃₉N₃O₅Si	573.764
——	7-[(3aS,4S,6R,6aR)-6-[(tert-butyl(diphenyl)silyl)oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]thieno[3,2-d]pyrimidin-4-amine	1370007-68-3	C₃₀H₃₅N₃O₄SSi	561.777
——	7-((3aS,4S,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3] dioxol-4-yl)furo[3,2-d]pyrimidin-4-amine	1370008-10-8	C₃₀H₃₅N₃O₅Si	545.711
——	3-(5'-O-tert-Butyldiphenylsilyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-6-(methylsulfanyl)imidazo[2,1-f][1,2,4]triazine	254114-44-8	C₃₀H₃₆N₄O₄SSi	576.792
——	7-((3aS,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-N-((S)-2,3-dihydro-1H-inden-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine	1370008-46-0	C₃₉H₄₄N₄O₄Si	660.888
——	3-(5'-O-tert-Butyldiphenylsilyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-6,8-bis(methylsulfanyl)imidazo[2,1-f][1,2,4]triazine	254114-42-6	C₃₁H₃₈N₄O₄S₂Si	622.885
——	3-(5'-O-tert-Butyldiphenylsilyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-8-hydrazino-6-(methylsulfanyl)imidazo[2,1-f][1,2,4]triazine	254114-43-7	C₃₀H₃₈N₆O₄SSi	606.821
——	7-((3aS,4S,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-N-((S)-2,3-dihydro-1H-inden-1-yl)thieno[3,2-d]pyrimidin-4-amine	1370007-73-0	C₃₉H₄₃N₃O₄SSi	677.94

反应信息

作为反应物：

描述：

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose 在 sodium hydride 、三乙胺、三氟乙酸作用下，以乙二醇二甲醚、二氯甲烷、氯仿、水、 N,N-二甲基甲酰胺、 mineral oil 为溶剂，反应 7.34h，生成 2-((3aS,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-3-(cyanomethylamino)acrylonitrile

参考文献：

名称：

SULFONAMIDE, SULFAMATE, AND SULFAMOTHIOATE DERIVATIVES

摘要：

该披露提供了化学式(I)的生物活性化合物及其药用盐，含有这些化合物的组合物，以及在各种应用中使用这些化合物的方法，例如用于治疗与E1型激活酶相关的疾病或紊乱，特别是与Nedd8激活酶(NAE)相关的疾病或紊乱。

公开号：

US20120077814A1
作为产物：

描述：

D-核糖在咪唑、盐酸、水、 copper(II) sulfate 作用下，以二氯甲烷为溶剂，反应 24.0h，生成 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

参考文献：

名称：

Synthesis of C-ribosyl imidazo[2,1-f ][1,2,4]triazines as inhibitors of adenosine and AMP deaminases

摘要：

新咪唑并[2,1-f][1,2,4]三嗪 27 的 3-β-D-ribofuranoside 6 与核苷脱氨基福尔马林 1 是同分异构体和等电子体，后者是腺苷脱氨酶 (ADA) 的良好抑制剂，而其 5′-monophosphate 2 则是腺苷 5′-monophosphate deaminase (AMPDA) 的良好抑制剂。6 的 6-甲硫基衍生物 7 是通过单环 1,2,4-三嗪 9 与溴醛 10 缩合合成的，缩合过程伴随着环化反应，从而得到受保护的 C 核苷 21；21 的 8-甲硫基通过肼置换和氧化作用去除。1,2,4-三嗪 9 与氯乙醛或其二甲基缩醛发生类似的环化反应，得到 6,8-双（甲硫基）咪唑并[2,1-f][1,2,4]三嗪 17，通过两种途径转化为母杂环 27，以及新环系统的单取代和二取代衍生物（19、20、24、25、28-30）。核苷 7 是哺乳动物 ADA 的抑制剂（IC50 40 µM）。

DOI：

10.1039/a904065j

点击查看最新优质反应信息

文献信息

Highly regioselective and stereoselective synthesis of C-Aryl glycosides via nickel-catalyzed ortho-C–H glycosylation of 8-aminoquinoline benzamides

作者：Wei-Yu Shi、Ya-Nan Ding、Nian Zheng、Xue-Ya Gou、Zhe Zhang、Xi Chen、Yu-Yong Luan、Zhi-Jie Niu、Yong-Min Liang

DOI：10.1039/d1cc03589d

日期：——

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzed ortho-CAr–H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C–H activation could be the rate-determining

C-芳基糖苷作为候选药物具有很高的价值。本文描述了一种新颖且经济高效的镍催化邻-C Ar -H 糖基化反应，具有高区域选择性和优异的 α-选择性。该方法与各种糖苷表现出良好的官能团相容性，显示出其合成潜力。机理研究表明 C-H 激活可能是速率决定步骤。
Synthesis of Cyclopentenyl Carbocyclic Nucleosides as Potential Antiviral Agents Against Orthopoxviruses and SARS

作者：Jong Hyun Cho、Dale L. Bernard、Robert W. Sidwell、Earl R. Kern、Chung K. Chu

DOI：10.1021/jm0509750

日期：2006.2.1

D-ribose (4). The key intermediate (+)-12a was utilized for the synthesis of unnatural five-membered ring heterocyclic carbocyclic nucleosides. The newly synthesized 1,2,3-triazole analogue (17c) exhibited potent antiviral activity (EC(50) 0.4 microM) against vaccinia virus and moderate activities (EC(50) 39 microM) against cowpox virus and severe acute respiratory syndrome coronavirus (SARSCoV) (EC(50)

已开发出一种实用且方便的合成手性环戊烯醇衍生物（+）-12a的方法，作为用于合成生物活性碳环核苷的关键中间体。选择性保护烯丙基羟基，然后与Grubbs催化剂进行闭环复分解（RCM）反应，可提供10 g规模的（+）-12a，D-核糖的总收率为52％（4）。关键中间体（+）-12a用于合成非天然的五元环杂环碳环核苷。新合成的1,2,3-三唑类似物（17c）对牛痘病毒显示有效的抗病毒活性（EC（50）0.4 microM），对牛痘病毒和严重的急性呼吸系统综合症冠状病毒（EC（50）39 microM）具有中等活性（EC（50）39 microM）（ SARSCoV）（EC（50）47 microM）。1,2
Synthesis and cancer growth inhibitory activities of 2-fatty-alkylated pyrrolidine-3,4-diol derivatives

作者：Pilar Elías-Rodríguez、Elena Moreno-Clavijo、Sebastián Carrión-Jiménez、Ana T. Carmona、Antonio J. Moreno-Vargas、Irene Caffa、Fabrizio Montecucco、Michele Cea、Alessio Nencioni、Inmaculada Robina

DOI：10.3998/ark.5550190.p008.492

日期：——

of new amphiphilic pyrrolidines containing dodecyl and oleyl apolar side chains were prepared and evaluated for their ability to inhibit the growth of pancreatic ductal adenocarcinoma cells in vitro. The new compounds are shown to exhibit anticancer activity at concentrations in the M range.

制备了一系列含有十二烷基和油基非极性侧链的新型两亲性吡咯烷，并评估了它们在体外抑制胰腺导管腺癌细胞生长的能力。新化合物在 M 范围内的浓度显示出抗癌活性。
Diastereoselective Synthesis of Aryl C ‐Glycosides from Glycosyl Esters via C−O Bond Homolysis

作者：Yongliang Wei、Benjamin Ben‐zvi、Tianning Diao

DOI：10.1002/anie.202014991

日期：2021.4.19

O‐ and N‐glycoside analogues. C‐aryl glycosides are extensively investigated as drug candidates and applied to chemical biology studies. Previously, C‐aryl glycosides were derived from lactones, glycals, glycosyl stannanes, and halides, via methods displaying various limitations with respect to the scope, functional‐group compatibility, and practicality. Challenges remain in the synthesis of C‐aryl

相对于O-和N-糖苷类似物， C-芳基糖基化合物具有更好的体内稳定性。C-芳基糖苷作为候选药物被广泛研究并应用于化学生物学研究。此前，C-芳基糖苷是从内酯、糖醛、糖基锡烷和卤化物衍生而来，其方法在范围、官能团兼容性和实用性方面存在各种局限性。从容易获得的碳水化合物前体合成C-芳基核苷和 2-脱氧糖仍然存在挑战。在此，我们报道了一种从糖基酯和溴芳烃制备C-芳基和杂芳基糖苷（包括核苷和2-脱氧糖）的交叉偶联方法。碳水化合物底物的激活利用二氢吡啶 (DHP) 作为激活基团，然后通过 CO 键均裂脱羧生成糖基自由基。该策略代表了一种激活醇作为交叉偶联伙伴的新方法。糖基酯的方便制备及其稳定性证明了该方法在药物化学中的潜力。
[EN] INTERMEDIATES AND METHODS FOR MAKING ZEARALENONE MACROLIDE ANALOGS [FR] INTERMÉDIAIRES ET PROCÉDÉS DE FABRICATION D'ANALOGUES MACROLIDES DE ZÉARALÉNONE

申请人：EISAI R&D MAN CO LTD

公开号：WO2009075818A1

公开（公告）日：2009-06-18

Disclosed herein are methods and intermediates useful in the preparation of macrolides, e.g., compounds of formula (IV) wherein R1-R12 are as defined herein.

本文披露了在制备大环内酯类化合物中有用的方法和中间体，例如，公式（IV）中R1-R12所定义的化合物。