1-<2,3-bis-O-(tert-butyldimethylsilyl)-4α-<(4,4'-dimethoxytrityl)oxymethyl>-β-D-ribo-pentofuranosyl>uracil

Base Information

Chemical Name:1-<2,3-bis-O-(tert-butyldimethylsilyl)-4α-<(4,4'-dimethoxytrityl)oxymethyl>-β-D-ribo-pentofuranosyl>uracil
CAS No.:232591-20-7
Molecular Formula:C₄₃H₆₀N₂O₉Si₂
Molecular Weight:805.128
Hs Code.:

Synonyms:1-<2,3-bis-O-(tert-butyldimethylsilyl)-4α-<(4,4'-dimethoxytrityl)oxymethyl>-β-D-ribo-pentofuranosyl>uracil

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Chemical Property of 1-<2,3-bis-O-(tert-butyldimethylsilyl)-4α-<(4,4'-dimethoxytrityl)oxymethyl>-β-D-ribo-pentofuranosyl>uracil

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Technology Process of 1-<2,3-bis-O-(tert-butyldimethylsilyl)-4α-<(4,4'-dimethoxytrityl)oxymethyl>-β-D-ribo-pentofuranosyl>uracil

There total 5 articles about 1-<2,3-bis-O-(tert-butyldimethylsilyl)-4α-<(4,4'-dimethoxytrityl)oxymethyl>-β-D-ribo-pentofuranosyl>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: 64.0%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 173846-42-9
1-<2,3-bis-O-(tert-butyldimethylsilyl)-4α-hydroxymethyl-β-D-ribo-pentofuranosyl>uracil

: 232591-20-7
1-<2,3-bis-O-(tert-butyldimethylsilyl)-4α-<(4,4'-dimethoxytrityl)oxymethyl>-β-D-ribo-pentofuranosyl>uracil

Guidance literature:: With pyridine; for 1.5h; Ambient temperature;
DOI:10.1021/jm990050i

Reference yield:

: 58-96-8
uridine

: 232591-20-7
1-<2,3-bis-O-(tert-butyldimethylsilyl)-4α-<(4,4'-dimethoxytrityl)oxymethyl>-β-D-ribo-pentofuranosyl>uracil

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 7 h / Ambient temperature

2: 59 percent / 80 percent AcOH, TFA / tetrahydrofuran / a) RT, 1 h, b) 0 deg C, 1.5 h

3: 24.6 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, pyridine, TFA / benzene; dimethylsulfoxide / 0.42 h / Ambient temperature

4: 1.) 2 M aq. NaOH, 2.) NaBH₄ / 1.) 1,4-dioxane, RT, 50 min, 2.) EtOH, 0 deg C, 30 min

5: 64 percent / pyridine / 1.5 h / Ambient temperature

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm990050i

Reference yield:

: 64898-15-3
2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine

: 232591-20-7
1-<2,3-bis-O-(tert-butyldimethylsilyl)-4α-<(4,4'-dimethoxytrityl)oxymethyl>-β-D-ribo-pentofuranosyl>uracil

Guidance literature:: Multi-step reaction with 4 steps

1: 59 percent / 80 percent AcOH, TFA / tetrahydrofuran / a) RT, 1 h, b) 0 deg C, 1.5 h

2: 24.6 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, pyridine, TFA / benzene; dimethylsulfoxide / 0.42 h / Ambient temperature

3: 1.) 2 M aq. NaOH, 2.) NaBH₄ / 1.) 1,4-dioxane, RT, 50 min, 2.) EtOH, 0 deg C, 30 min

4: 64 percent / pyridine / 1.5 h / Ambient temperature

With pyridine; sodium hydroxide; sodium tetrahydroborate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; dimethyl sulfoxide; benzene;
DOI:10.1021/jm990050i