1,3,5-tri-O-acetyl-3-C-<(tert-butyldiphenyl)siloxymethyl>-3-deoxy-D-ribofuranose

Base Information

Chemical Name:1,3,5-tri-O-acetyl-3-C-<(tert-butyldiphenyl)siloxymethyl>-3-deoxy-D-ribofuranose
CAS No.:241817-08-3
Molecular Formula:C₂₈H₃₆O₈Si
Molecular Weight:528.675
Hs Code.:

Synonyms:1,3,5-tri-O-acetyl-3-C-<(tert-butyldiphenyl)siloxymethyl>-3-deoxy-D-ribofuranose

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Chemical Property of 1,3,5-tri-O-acetyl-3-C-<(tert-butyldiphenyl)siloxymethyl>-3-deoxy-D-ribofuranose

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Technology Process of 1,3,5-tri-O-acetyl-3-C-<(tert-butyldiphenyl)siloxymethyl>-3-deoxy-D-ribofuranose

There total 1 articles about 1,3,5-tri-O-acetyl-3-C-<(tert-butyldiphenyl)siloxymethyl>-3-deoxy-D-ribofuranose 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: 84.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1,3,5-tri-O-acetyl-3-deoxy-3-C-hydroxymethyl-D-ribofuranose

: 241817-08-3
1,3,5-tri-O-acetyl-3-C-<(tert-butyldiphenyl)siloxymethyl>-3-deoxy-D-ribofuranose

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 2h; Ambient temperature;
DOI:10.1016/S0968-0896(99)00061-9

Reference yield: 62.0%

: 241817-08-3
1,3,5-tri-O-acetyl-3-C-<(tert-butyldiphenyl)siloxymethyl>-3-deoxy-D-ribofuranose

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

: 241817-10-7
1-<2,5-di-O-acetyl-3-C-(tert-butyldiphenyl)siloxymethyl-3-deoxy-β-D-erythro-pentofuranosyl>thymine

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1.) room temperature, overnight, 2.) 50 deg C, 24 h;
DOI:10.1016/S0968-0896(99)00061-9

Reference yield:

: 241817-08-3
1,3,5-tri-O-acetyl-3-C-<(tert-butyldiphenyl)siloxymethyl>-3-deoxy-D-ribofuranose

: 1-<3-deoxy-5-O-dimethoxytrityl-3-C-hydroxymethyl-2-O-(2-methoxyethoxymethyl)-β-D-erythro-pentofuranosyl>thymine 2-cyanoethyl N,N-diisopropylphosphoramidite

Guidance literature:: Multi-step reaction with 9 steps

1: 62 percent / TMSOTf / CH₂Cl₂ / 1.) room temperature, overnight, 2.) 50 deg C, 24 h

2: 70 percent / pyridine / 80 °C

3: 74 percent / K₂CO₃ / methanol / 0.5 h / -5 °C

4: 63 percent / pyridine / 0.67 h / -5 °C

5: 75 percent / i-Pr₂NEt / CH₂Cl₂ / 48 h / 50 °C

6: 100 percent / NH₃/MeOh / 48 h / Ambient temperature

7: pyridine / 24 h / Ambient temperature

8: TBAF / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h

9: 61 percent / i-Pr₂NEt / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; ammonia; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0968-0896(99)00061-9