6-[(tert-butyldiphenylsilyloxy)methyl]-2',3'-O-isopropylideneuridine 5'-carboxaldehyde

Base Information

Chemical Name:6-[(tert-butyldiphenylsilyloxy)methyl]-2',3'-O-isopropylideneuridine 5'-carboxaldehyde
CAS No.:325705-81-5
Molecular Formula:C₂₉H₃₄N₂O₇Si
Molecular Weight:550.684
Hs Code.:

Synonyms:6-[(tert-butyldiphenylsilyloxy)methyl]-2',3'-O-isopropylideneuridine 5'-carboxaldehyde

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Chemical Property of 6-[(tert-butyldiphenylsilyloxy)methyl]-2',3'-O-isopropylideneuridine 5'-carboxaldehyde

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Technology Process of 6-[(tert-butyldiphenylsilyloxy)methyl]-2',3'-O-isopropylideneuridine 5'-carboxaldehyde

There total 6 articles about 6-[(tert-butyldiphenylsilyloxy)methyl]-2',3'-O-isopropylideneuridine 5'-carboxaldehyde 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: 80.0%

: 325705-80-4
6-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneuridine

: 325705-81-5
6-[(tert-butyldiphenylsilyloxy)methyl]-2',3'-O-isopropylideneuridine 5'-carboxaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 23 ℃; for 4h;
DOI:10.1016/S0040-4020(00)00970-4

Reference yield:

: 102147-76-2
5'-O-(t-butyldimethylsilyl)-2',3'-O-isopropylideneuridine

: 325705-81-5
6-[(tert-butyldiphenylsilyloxy)methyl]-2',3'-O-isopropylideneuridine 5'-carboxaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: (i-Pr)2NH; BuLi / hexane; tetrahydrofuran / 2.5 h / -76 °C

1.2: hexane; tetrahydrofuran / 2.5 h / -76 °C

1.3: 85 percent / NaBH₄ / hexane; tetrahydrofuran; ethanol / 5.5 h / 26 °C

2.1: 59 percent / 1H-imidazole; DMAP / CH₂Cl₂ / 6 h / 26 °C

3.1: 99 percent / H₂SiF₆ / acetonitrile; H₂O; 2-methyl-propan-2-ol / 3 h / 0 °C

4.1: 0.97 g / DCC; CHCl₂CO₂H; DMSO / 3 h / 25 °C

With 1H-imidazole; dichloro-acetic acid; dmap; n-butyllithium; fluorosilicic acid; dimethyl sulfoxide; diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 4.1: Pfitzner-Moffatt oxidation;
DOI:10.1002/hlca.200690259

Reference yield:

: 195449-53-7
5'-O-[(tert-butyl)dimethylsilyl]-6-(hydroxymethyl)-2',3'-O-isopropylideneuridine

: 325705-81-5
6-[(tert-butyldiphenylsilyloxy)methyl]-2',3'-O-isopropylideneuridine 5'-carboxaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 59 percent / 1H-imidazole; DMAP / CH₂Cl₂ / 6 h / 26 °C

2: 99 percent / H₂SiF₆ / acetonitrile; H₂O; 2-methyl-propan-2-ol / 3 h / 0 °C

3: 0.97 g / DCC; CHCl₂CO₂H; DMSO / 3 h / 25 °C

With 1H-imidazole; dichloro-acetic acid; dmap; fluorosilicic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In dichloromethane; water; acetonitrile; tert-butyl alcohol; 3: Pfitzner-Moffatt oxidation;
DOI:10.1002/hlca.200690259