3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

Base Information

Chemical Name:3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester
CAS No.:252001-19-7
Molecular Formula:C₄₃H₆₇N₅O₁₂Si₃
Molecular Weight:930.288
Hs Code.:

3-{[5-(6-benzoylamino-purin-9-yl)-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

Synonyms:3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

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Chemical Property of 3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

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Technology Process of 3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

There total 16 articles about 3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 252001-18-6
methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate

: 252000-89-8
N⁶-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)adenine

: 3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

: 252001-19-7
3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

Guidance literature:: methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate; With samarium diiodide; In tetrahydrofuran; at -78 ℃;

N⁶-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)adenine; In tetrahydrofuran; Title compound not separated from byproducts;
DOI:10.1021/ja992608h

Reference yield:

: 28990-73-0
9-(2-O-methyl-5-O-trityl-β-D-ribofluranosyl)adenine

: 252001-19-7
3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: CrO₃; Ac₂O; pyridine / CH₂Cl₂ / 0 °C

2.1: NaBH₄; AcOH / 12 h / 4 °C

3.1: imidazole / dimethylformamide / 15 h / 20 °C

4.1: pyridine / 3 h / 20 °C

5.1: 81 percent / 80 percent aq. TFA / CH₂Cl₂ / 1 h / 20 °C

6.1: DCC; DMSO; CF₃COOH / pyridine / 2 h / 20 °C

7.1: SmI₂ / tetrahydrofuran / -78 °C

7.2: tetrahydrofuran

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium tetrahydroborate; samarium diiodide; acetic anhydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; 1.1: Oxidation / 2.1: Reduction / 3.1: silylation / 4.1: Acylation / 5.1: trityl deprotection / 6.1: Oxidation / 7.1: Metallation / 7.2: Addition;
DOI:10.1021/ja992608h

Reference yield:

: 69304-37-6
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

: 252001-19-7
3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: pyridine

1.2: 59 percent / p-TsOH / dimethylformamide

2.1: pyridine

4.1: TFA / CH₂Cl₂

5.1: DCC; DMSO; TFA / dimethylsulfoxide

5.2: 61 percent / PDC / dimethylformamide

6.1: K₂CO₃ / methanol

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

8.1: SmI₂ / tetrahydrofuran / -78 °C

8.2: tetrahydrofuran

With pyridine; samarium diiodide; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1.1: silylation / 1.2: Isomerization / 2.1: Etherification / 3.1: Acetylation / 4.1: deprotection / 5.1: Moffatt oxidation / 5.2: Oxidation / 6.1: Hydrolysis / 7.1: Swern oxidation / 8.1: Metallation / 8.2: Addition;
DOI:10.1021/ja992608h