1-[(2R,4S,5R)-5-(3-Bromo-prop-1-ynyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,4S,5R)-5-(3-Bromo-prop-1-ynyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 181999-92-8
• Molecular Formula: C₂₈H₃₁BrN₂O₄Si
• Molecular Weight: 567.555

Synonyms:1-[(2R,4S,5R)-5-(3-Bromo-prop-1-ynyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property of 1-[(2R,4S,5R)-5-(3-Bromo-prop-1-ynyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property:

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Technology Process of 1-[(2R,4S,5R)-5-(3-Bromo-prop-1-ynyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

There total 2 articles about 1-[(2R,4S,5R)-5-(3-Bromo-prop-1-ynyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 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: 71.0%

1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(3-hydroxy-prop-1-ynyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (181999-85-9) → 1-[(2R,4S,5R)-5-(3-Bromo-prop-1-ynyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (181999-92-8)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/0040-4039(96)01164-1

Reference yield:

1-(2,5,6-trideoxy-6,6-dibromo-3-O-(tert-butyldiphenylsilyl)-β-D-erythro-hex-5-enofuranosyl)-5-methyluracil (181999-83-7) → 1-[(2R,4S,5R)-5-(3-Bromo-prop-1-ynyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (181999-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / BuLi / -78 - 25 °C

2: 71 percent / CBr₄, Ph₃P / CH₂Cl₂ / 1 h / 0 °C

With n-butyllithium; carbon tetrabromide; triphenylphosphine; In dichloromethane;

DOI:10.1016/0040-4039(96)01164-1

Reference yield: 51.0%

1-[(2R,4S,5R)-5-(3-Bromo-prop-1-ynyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (181999-92-8) + 1-{(2R,4S,5R)-4-Mercapto-5-[tris-(4-tert-butyl-phenyl)-methoxymethyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione → C69H82N4O8SSi (181999-94-0)

Guidance literature:

With 18-crown-6 ether; sodium hydrogencarbonate; In diethyl ether; for 12h;

DOI:10.1016/0040-4039(96)01164-1

upstream raw materials:

1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(3-hydroxy-prop-1-ynyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

1-(2,5,6-trideoxy-6,6-dibromo-3-O-(tert-butyldiphenylsilyl)-β-D-erythro-hex-5-enofuranosyl)-5-methyluracil

Downstream raw materials:

C₆₉H₈₂N₄O₈SSi

C₅₃H₆₄N₄O₈S

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