6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo//α-L-talo-hept-6-ynofuranosyl]uracil

Base Information

Chemical Name:6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo//α-L-talo-hept-6-ynofuranosyl]uracil
CAS No.:928034-56-4
Molecular Formula:C₃₇H₅₀N₂O₇Si₂
Molecular Weight:690.984
Hs Code.:

6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo//α-L-talo-hept-6-ynofuranosyl]uracil

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Chemical Property of 6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo//α-L-talo-hept-6-ynofuranosyl]uracil

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Technology Process of 6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo//α-L-talo-hept-6-ynofuranosyl]uracil

There total 6 articles about 6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo//α-L-talo-hept-6-ynofuranosyl]uracil 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:

: 1777-03-3
2-triethylsilylacetylene

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

: 928034-56-4
6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo//α-L-talo-hept-6-ynofuranosyl]uracil

Guidance literature:: With ethylmagnesium bromide; In tetrahydrofuran; at -15 ℃; for 2h;
DOI:10.1002/hlca.200690259

Reference yield:

: 362-43-6
2',3'-O-isopropylideneuridine

: 928034-56-4
6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo//α-L-talo-hept-6-ynofuranosyl]uracil

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / 1H-imidazole; DMAP / CH₂Cl₂ / 12 h / 24 °C

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

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

2.3: 85 percent / NaBH₄ / hexane; tetrahydrofuran; ethanol / 5.5 h / 26 °C

3.1: 59 percent / 1H-imidazole; DMAP / CH₂Cl₂ / 6 h / 26 °C

4.1: 99 percent / H₂SiF₆ / acetonitrile; H₂O; 2-methyl-propan-2-ol / 3 h / 0 °C

5.1: 0.97 g / DCC; CHCl₂CO₂H; DMSO / 3 h / 25 °C

6.1: 793 mg / EtMgBr / tetrahydrofuran / 2 h / -15 °C

With 1H-imidazole; dichloro-acetic acid; dmap; n-butyllithium; fluorosilicic acid; ethylmagnesium bromide; dimethyl sulfoxide; diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 5.1: Pfitzner-Moffatt oxidation;
DOI:10.1002/hlca.200690259

Reference yield:

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

: 928034-56-4
6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo//α-L-talo-hept-6-ynofuranosyl]uracil

Guidance literature:: Multi-step reaction with 5 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

5.1: 793 mg / EtMgBr / tetrahydrofuran / 2 h / -15 °C

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