1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]uracil

Base Information

• Chemical Name: 1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]uracil
• CAS No.: 132364-17-1
• Molecular Formula: C₂₅H₂₈N₂O₄Si
• Molecular Weight: 448.594

Synonyms:1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]uracil

Chemical Property of 1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]uracil

Chemical Property:

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SDS file from LookChem

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Technology Process of 1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]uracil

There total 32 articles about 1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]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: 100.0%

1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (132336-21-1) → 1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]uracil (132364-17-1)

Guidance literature:

With tributyl-amine; In xylene; for 1.5h; Heating; or DBU;

DOI:10.1246/cl.1990.1459

Reference yield: 94.0%

1-[(3aR,4R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-thioxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1H-pyrimidine-2,4-dione → 1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]uracil (132364-17-1)

Guidance literature:

With triethyl phosphite; at 110 ℃; for 17h;

DOI:10.1021/jo980975q

Reference yield: 73.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 2',3'-dideoxy-2',3'-didehydrouridine (5974-93-6) → 1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]uracil (132364-17-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 18h;

DOI:10.1021/jm050111e

upstream raw materials:

1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

benzaldehyde

1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-xylofuranosyl>uracil

isobutyraldehyde

Downstream raw materials:

5-[(S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-pentyl]-1H-pyrimidine-2,4-dione

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