(2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-4-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran

Base Information

Chemical Name:(2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-4-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran
CAS No.:296250-74-3
Molecular Formula:C₃₈H₄₈N₂O₈Si
Molecular Weight:688.893
Hs Code.:

Synonyms:(2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-4-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran

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Chemical Property of (2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-4-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran

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Technology Process of (2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-4-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran

There total 12 articles about (2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-4-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran 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: 68.6%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 296250-73-2
(2S,3S,4R)-3,4-dihydroxy-4-(4,4'-dimethoxytrityl)oxymethyl-2-((thymin-1-yl)methyl)tetrahydrofuran

: 296250-74-3
(2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-4-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 72h;
DOI:10.1021/jo000275x

Reference yield:

: 153186-10-8
((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

: 296250-74-3
(2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-4-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 12 steps

1: pyridine / 0.33 h / 20 °C

2: 11.896 g / aq. HCl / 10 h

3: NaH / dimethylformamide / 2 h / 20 °C

4: aq. AcOH / 3.5 h / 50 °C

5: 5.776 g / NaBH₄ / methanol / 0.33 h / 20 °C

6: 82.8 percent / DMAP / CH₂Cl₂ / 10 h / 20 °C

7: 84.2 percent / DMAP / pyridine / 2 h / 20 °C

8: 51.6 percent / NaH / dimethylformamide / 4 h / 120 °C

9: 87.4 percent / H₂ / Pd(OH)2/C / ethanol / 36 h / 20 °C

10: 81.6 percent / MeONa / methanol / 0.83 h / 0 °C

11: 87 percent / pyridine / 2 h / 20 °C

12: 68.6 percent / imidazole / CH₂Cl₂ / 72 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; hydrogen; sodium methylate; sodium hydride; acetic acid; palladium dihydroxide; In pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: sulfonation / 2: Hydrolysis / 3: Cyclization / 4: Hydrolysis / 5: Reduction / 6: Tosylation / 7: Acetylation / 8: Substitution / 9: Hydrogenolysis / 10: ester cleavage / 11: Alkylation / 12: silylation;
DOI:10.1021/jo000275x

Reference yield:

: 223591-10-4
(2R,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-formyl-4-hydroxytetrahydrofuran

: 296250-74-3
(2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-4-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 8 steps

1: 5.776 g / NaBH₄ / methanol / 0.33 h / 20 °C

2: 82.8 percent / DMAP / CH₂Cl₂ / 10 h / 20 °C

3: 84.2 percent / DMAP / pyridine / 2 h / 20 °C

4: 51.6 percent / NaH / dimethylformamide / 4 h / 120 °C

5: 87.4 percent / H₂ / Pd(OH)2/C / ethanol / 36 h / 20 °C

6: 81.6 percent / MeONa / methanol / 0.83 h / 0 °C

7: 87 percent / pyridine / 2 h / 20 °C

8: 68.6 percent / imidazole / CH₂Cl₂ / 72 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; hydrogen; sodium methylate; sodium hydride; palladium dihydroxide; In pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Tosylation / 3: Acetylation / 4: Substitution / 5: Hydrogenolysis / 6: ester cleavage / 7: Alkylation / 8: silylation;
DOI:10.1021/jo000275x