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

Base Information

• Chemical Name: 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
• CAS No.: 129678-63-3
• Molecular Formula: C₂₉H₃₇N₃O₅S₂Si
• Molecular Weight: 599.847
• Mol file: 129678-63-3.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 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

There total 3 articles about 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 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: 62.0%

1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>uracil (130351-52-9) + tert-butylchlorodiphenylsilane (58479-61-1) → 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)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; Ambient temperature;

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) → 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)

Guidance literature:

Multi-step reaction with 3 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

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; triethylamine; trifluoroacetic acid; In N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/jm00171a025

Reference yield:

1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-5-O-trityl-β-D-arabino-pentofuranosyl>uracil (130351-51-8) → 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)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature

With dmap; triethylamine; trifluoroacetic acid; In N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/jm00171a025

upstream raw materials:

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

tert-butylchlorodiphenylsilane

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

(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

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

(E)-5-(2-bromovinyl)-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil