(2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-carbaldehyde

Base Information

• Chemical Name: (2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-carbaldehyde
• CAS No.: 129678-52-0
• Molecular Formula: C₂₆H₃₀N₂O₆Si
• Molecular Weight: 494.62
• Mol file: 129678-52-0.mol

Synonyms:(2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-carbaldehyde

Chemical Property of (2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-carbaldehyde

There total 4 articles about (2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-carbaldehyde 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: 85.0%

1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>uracil (129678-63-3) → (2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-carbaldehyde (129678-52-0)

Guidance literature:

With mercury dichloride; mercury(II) oxide; In tetrahydrofuran; water; at 0 ℃; for 0.0833333h;

DOI:10.1021/jm00171a025

Reference yield:

1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>uracil (130351-52-9) → (2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-carbaldehyde (129678-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature

2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 °C

With dmap; triethylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00171a025

Reference yield:

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione (96253-10-0) → (2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-carbaldehyde (129678-52-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min

2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature

3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature

4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; triethylamine; trifluoroacetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/jm00171a025

upstream raw materials:

1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>uracil

1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>uracil

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione

1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-5-O-trityl-β-D-arabino-pentofuranosyl>uracil

Downstream raw materials:

1-<5-O-(tert-butyldiphenylsilyl)-2,3-didehydro-2,3-dideoxy-3-C-formyl-β-D-glycero-pent-2-eno-furanosyl>uracil

1-<2-O-acetyl-3-C-(acetyloxymethylene)-5-O-(tert-butyldiphenylsilyl)-3-deoxy-β-D-arabino-pentofuranosyl>uracil

1-(3-deoxy-3-C-formyl-β-D-lyxo-pentofuranosyl)uracil 3',5'-O-hemiacetal

1-[(2R,3S,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione