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

Base Information

• Chemical Name: 1-(2,5,6-trideoxy-6,6-dibromo-3-O-(tert-butyldiphenylsilyl)-β-D-erythro-hex-5-enofuranosyl)-5-methyluracil
• CAS No.: 181999-83-7
• Molecular Formula: C₂₇H₃₀Br₂N₂O₄Si
• Molecular Weight: 634.44
• Mol file: 181999-83-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 1-(2,5,6-trideoxy-6,6-dibromo-3-O-(tert-butyldiphenylsilyl)-β-D-erythro-hex-5-enofuranosyl)-5-methyluracil 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: 80.0%

(dibromomethyl)(triphenyl)phosphonium bromide (56506-90-2) + 1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil (146604-43-5) → 1-(2,5,6-trideoxy-6,6-dibromo-3-O-(tert-butyldiphenylsilyl)-β-D-erythro-hex-5-enofuranosyl)-5-methyluracil (181999-83-7)

Guidance literature:

With zinc; In 1,4-dioxane; for 3h; Reflux;

DOI:10.1016/j.bioorg.2011.03.002

Reference yield: 75.0%

carbon tetrabromide (558-13-4) + 1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil (146604-43-5) → 1-(2,5,6-trideoxy-6,6-dibromo-3-O-(tert-butyldiphenylsilyl)-β-D-erythro-hex-5-enofuranosyl)-5-methyluracil (181999-83-7)

Guidance literature:

carbon tetrabromide; With triphenylphosphine; In dichloromethane; at 0 ℃; for 0.333333h;

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil; In dichloromethane; at 0 ℃; for 3h; Further stages.;

DOI:10.1021/ol0166045

Reference yield:

6′-dibromo-(5′-deoxy-5′-methylidene)-3′-O-(tert-butyldiphenylsilyl)-3-(2-trimethylsilylethoxymethyl)thymidine → 1-(2,5,6-trideoxy-6,6-dibromo-3-O-(tert-butyldiphenylsilyl)-β-D-erythro-hex-5-enofuranosyl)-5-methyluracil (181999-83-7)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 0 - 20 ℃; for 9h; Inert atmosphere;

DOI:10.1021/acs.joc.9b01318

upstream raw materials:

carbon tetrabromide

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine

Downstream 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

(E)-6'-bromo-(5'-deoxy-5'-methylidene)-3'-O-(tert-bytuldiphenylsilyl)thymidine

C₂₇H₃₀N₂O₄Si

1-[(2R,4S,5S)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-(4-{(2R,3S,5R)-3-hydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-2-yl}-1H-1,2,3-triazol-1-yl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione