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喹啉
水杨醛
二溴甲烷
谷胱甘肽
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1-((6aR,8R,9R,9aR)-2,2,4,4-tetraisopropyl-9-((trimethylsilyl)oxy)tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione | 415903-48-9

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

1-((6aR,8R,9R,9aR)-2,2,4,4-tetraisopropyl-9-((trimethylsilyl)oxy)tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione

英文别名

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)uridine；2'-O-trimethylsilyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxanediyl)uridine

1-((6aR,8R,9R,9aR)-2,2,4,4-tetraisopropyl-9-((trimethylsilyl)oxy)tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione化学式

CAS

415903-48-9

化学式

C₂₄H₄₆N₂O₇Si₃

mdl

——

分子量

558.895

InChiKey

GTZFWOGCBHFWBS-JMJGKCIBSA-N

BEILSTEIN

——

EINECS

——

物化性质

密度：

1.10±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

4.61
重原子数：

36.0
可旋转键数：

7.0
环数：

3.0
sp3杂化的碳原子比例：

0.83
拓扑面积：

101.01
氢给体数：

1.0
氢受体数：

8.0

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
3',5'-O-(1,1,3,3-四异丙基-1,3-二硅氧烷)尿苷	3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine	69304-38-7	C₂₁H₃₈N₂O₇Si₂	486.713
尿嘧啶核苷	uridine	58-96-8	C₉H₁₂N₂O₆	244.204

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	3-methyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)uridine	415903-50-3	C₂₅H₄₈N₂O₇Si₃	572.922
——	3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methyluridine	83167-64-0	C₂₂H₄₀N₂O₇Si₂	500.74
——	3-methyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)uridine	415903-53-6	C₂₂H₄₀N₂O₇Si₂	500.74
——	N³-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)uridine	195247-12-2	C₂₇H₄₈N₂O₉Si₂	600.857
——	2'-O-[bis(2-acetoxyethoxy)methyl]-3-methyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)uridine	415903-63-8	C₃₁H₅₄N₂O₁₃Si₂	718.946
——	3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-methylcytidine	97626-19-2	C₂₂H₄₁N₃O₆Si₂	499.755
——	4-N-methyl-3',5'-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine	110588-51-7	C₂₃H₄₃N₃O₆Si₂	513.782
——	4,4-N,N-dimethyl-3',5'-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine	110567-20-9	C₂₄H₄₅N₃O₆Si₂	527.809
——	N³-benzoyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine	86988-35-4	C₂₈H₄₂N₂O₈Si₂	590.821
——	3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N3-(4-tert-butylbenzoyl)uridine	163071-12-3	C₃₂H₅₀N₂O₈Si₂	646.929
——	2,2-Dimethyl-propionic acid 3-{(2R,3R,3aR,9aR)-3-[1-(2-fluoro-phenyl)-4-methoxy-piperidin-4-yloxy]-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl}-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester	195247-15-5	C₃₉H₆₂FN₃O₁₀Si₂	808.105
——	1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-4-(2-nitrophenyl)-2-pyrimidinone	108782-90-7	C₂₇H₄₁N₃O₉Si₂	607.808
——	1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-2'-O-methyl-4-(2-nitrophenyl)-2-pyrimidinone	110567-19-6	C₂₈H₄₃N₃O₉Si₂	621.835
——	5'-O-[benzhydryloxy-bis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methyluridine	415903-59-2	C₃₈H₅₆N₂O₁₅Si₃	865.124
尿嘧啶核苷	uridine	58-96-8	C₉H₁₂N₂O₆	244.204
2'-甲氧基尿苷	2'-O-methyluridine	2140-76-3	C₁₀H₁₄N₂O₆	258.231
——	2'-O-[bis(2-acetoxyethoxy)methyl]-3-methyluridine	415903-56-9	C₁₉H₂₈N₂O₁₂	476.438
2',3',5'-三乙酰尿苷	Tri-O-acetyluridine	4105-38-8	C₁₅H₁₈N₂O₉	370.316
——	3-N-pivaloyloxymethyl-2'-O-(9-phenylxanthen-9-yl)-5'-O-(tert-butoxydiphenylsilyl)uridine	195247-38-2	C₅₀H₅₂N₂O₁₀Si	869.056
——	3-N-pivaloyloxymethyl-2'-O-(9-phenylxanthen-9-yl)uridine	195247-37-1	C₃₄H₃₄N₂O₉	614.652
——	3-N-pivaloyloxymethyl-2'-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl]-3'-O-(9-phenylxanthen-9-yl)uridine	195247-18-8	C₄₆H₄₈FN₃O₁₀	821.9
——	N3-(4-tert-butylbenzoyl)-2'-O-allyluridine	163071-13-4	C₂₃H₂₈N₂O₇	444.485
——	5'-O-dimethoxytrityl-N3-(4-tert-butylbenzoyl)-2'-O-allyluridine	163071-14-5	C₄₄H₄₆N₂O₉	746.857
胞苷	CYTIDINE	65-46-3	C₉H₁₃N₃O₅	243.219
2'-甲氧基胞苷	2'-O-methylcytidine	2140-72-9	C₁₀H₁₅N₃O₅	257.246
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-oxo-4-phenylsulfanyl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester	108324-72-7	C₂₁H₂₂N₂O₈S	462.48
——	1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(2-oxo-2H-pyridin-1-yl)-1H-pyrimidin-2-one	111426-23-4	C₁₄H₁₅N₃O₆	321.29
N4-甲基胞苷	N⁴-methylcytidine	10578-79-7	C₁₀H₁₅N₃O₅	257.246
N,N-二甲基-2'-O-甲基胞苷	N4,N4,2’-O-trimethylcytidine	34218-81-0	C₁₂H₁₉N₃O₅	285.3
N,2'-O-二甲基胞苷	N4,2'-O-dimethylcytidine	13048-95-8	C₁₁H₁₇N₃O₅	271.273
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-dimethylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester	98222-28-7	C₁₇H₂₃N₃O₈	397.385
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-oxo-4-p-tolylsulfanyl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester	99519-13-8	C₂₂H₂₄N₂O₈S	476.507
——	2',3',5'-tri-O-acetyl-N⁴-methyl-cytidine	111426-20-1	C₁₆H₂₁N₃O₈	383.358
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-morpholin-4-yl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester	111426-19-8	C₁₉H₂₅N₃O₉	439.422
——	1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(pyridin-2-ylsulfanyl)-1H-pyrimidin-2-one	111426-26-7	C₁₄H₁₅N₃O₅S	337.356
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-oxo-4-(4-oxo-4H-pyridin-1-yl)-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester	108324-74-9	C₂₀H₂₁N₃O₉	447.401
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-oxo-4-(2-oxo-2H-pyridin-1-yl)-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester	108324-73-8	C₂₀H₂₁N₃O₉	447.401
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-oxo-4-(pyridin-2-ylsulfanyl)-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester	108324-71-6	C₂₀H₂₁N₃O₈S	463.468
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-oxo-4-(pyridin-2-yloxy)-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester	108324-68-1	C₂₀H₂₁N₃O₉	447.401
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-oxo-4-(pyridin-3-yloxy)-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester	108324-69-2	C₂₀H₂₁N₃O₉	447.401
——	1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(pyridin-3-yloxy)-1H-pyrimidin-2-one	111426-25-6	C₁₄H₁₅N₃O₆	321.29
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[4-(6-methyl-pyridin-3-yloxy)-2-oxo-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester	108324-70-5	C₂₁H₂₃N₃O₉	461.428
——	1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(6-methyl-pyridin-3-yloxy)-1H-pyrimidin-2-one	108782-91-8	C₁₅H₁₇N₃O₆	335.316
——	Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[4-(6-methyl-pyridin-2-yloxy)-2-oxo-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester	108348-48-7	C₂₁H₂₃N₃O₉	461.428
——	1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(6-methyl-pyridin-2-yloxy)-1H-pyrimidin-2-one	111426-24-5	C₁₅H₁₇N₃O₆	335.316

反应信息

作为反应物：

描述：

1-((6aR,8R,9R,9aR)-2,2,4,4-tetraisopropyl-9-((trimethylsilyl)oxy)tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione 在三乙烯二胺、 4-二甲氨基吡啶、 2,4,6-三甲基苯磺酰氯、四丁基氟化铵、氨、三乙胺作用下，以四氢呋喃、甲醇为溶剂，反应 7.08h，生成胞苷

参考文献：

名称：

Zhou; Welch; Chattopadhyaya, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816

摘要：

DOI：
作为产物：

描述：

尿嘧啶核苷在三乙胺作用下，以吡啶、二氯甲烷为溶剂，反应 9.5h，生成 1-((6aR,8R,9R,9aR)-2,2,4,4-tetraisopropyl-9-((trimethylsilyl)oxy)tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione

参考文献：

名称：

3-甲基尿苷亚磷酰胺的合成以研究甲基化在核糖体RNA发夹中的作用。

摘要：

据报道，合成了5'-O-BzH-2'-O-ACE-保护的3-甲基尿苷亚磷酰胺[BzH，苯甲酰氧基-双（三甲基甲硅烷基氧基）甲硅烷基； [BzH]。ACE，双（2-乙酰氧基乙氧基）甲基]。亚磷酰胺用于固相RNA合成，以生成一系列包含单个或多个修饰的RNA发夹，包括常见的核苷伪尿苷。生成了三个代表大肠杆菌23S核糖体RNA的1920环区域（G（1906）-C（1924））的19个核苷酸的发夹RNA。分别在1911、1915和1917位进行了修饰。通过热解，圆二色性和NMR光谱检查了这三种RNA的稳定性和结构。

DOI：

10.1016/s0968-0896(01)00283-8

点击查看最新优质反应信息

文献信息

An Improved Transient Method for the Synthesis ofN-Benzoylated Nucleosides

作者：Xue-Feng Zhu、Howard J. Williams、A. Ian Scott

DOI：10.1081/scc-120017200

日期：2003.1.5

The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.
Trimethylsilyl Trifluoromethanesulfonate-promoted Reductive 2′-O-arylmethylation of Ribonucleoside Derivatives

作者：Naoki Uchiyama、Toshihiko Ogata、Natsuhisa Oka、Takeshi Wada

DOI：10.1080/15257770.2011.592171

日期：2011.6.1

Arylmethyl groups such as benzyl, p-methoxybenzyl, and 1-pyrenylmethyl groups were introduced to the 2'-O-position of nucleosides by reductive etherification. Combining corresponding aromatic aldehydes with 2'-O-trimethylsilylnucleoside derivatives in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) resulted in moderate to good yields of the 2'-O-arylmethyluridine derivatives, whereas the corresponding cytidine and adenosine derivatives were obtained in low yields. The reaction of ribonucleosides with aliphatic aldehydes did not proceed smoothly. Anomerization of the uridine derivatives by TMSOTf was observed in CH(2)Cl(2), toluene, and CH(3)CN, but was completely suppressed when the reactions were conducted in 1,4-dioxane.
Simplified and Cost Effective Syntheses of Fully Protected Phosphoramidite Monomers Suitable for the Assembly of Oligo(2′-O-allylribonucleotides)

作者：Barbro Beijer、Morten Gr⊘tli、Mark E. Douglas、Brian S. Sproat

DOI：10.1080/15257779408010672

日期：1994.9

Simplified, high yielding syntheses of suitably protected 2'-O-allylribonucleoside-3'-O-phosphoramidites starting from standard ribonucleosides have been elucidated. Specific 2'-O-allylation is readily achieved using amidine protection of the exocyclic amino groups of adenosine and cytidine and in the case of guanosine the allylation is carried out on an easily prepared intermediate bearing transient protection of the lactam function.
Nyilas; Chattopadhyaya, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 826 - 830

作者：Nyilas、Chattopadhyaya

DOI：——

日期：——
Solid-phase synthesis of branched RNA and branched DNA/RNA chimeras

作者：Morten Grøtli、Ramon Eritja、Brian Sproat

DOI：10.1016/s0040-4020(97)00731-x

日期：1997.8

An effective method for synthesising branched oligonucleotides on solid phase in the 5' to 3' direction has been developed. Special branch-point monomers enable the synthesis of branched oligonucleotides which can have sequences of different length and base composition attached to the 2'-and 3'-hydroxyl groups of the branch point ribonucleoside. The branched oligonucleotides are assembled on commercial DNA synthesisers, the crude products are readily purified by reversed phase HPLC and the fully deprotected products are conveniently analysed by mass spectrometry. (C) 1997 Elsevier Science Ltd.