3-N-benzyloxymethyl-1-[(1S)-1-phenyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2,3-hexodiulofuranosyl]uracil

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Chemical Name:3-N-benzyloxymethyl-1-[(1S)-1-phenyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2,3-hexodiulofuranosyl]uracil
CAS No.:476490-37-6
Molecular Formula:C₃₆H₅₀N₂O₉Si₂
Molecular Weight:710.972
Hs Code.:

Synonyms:3-N-benzyloxymethyl-1-[(1S)-1-phenyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2,3-hexodiulofuranosyl]uracil

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Chemical Property of 3-N-benzyloxymethyl-1-[(1S)-1-phenyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2,3-hexodiulofuranosyl]uracil

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Technology Process of 3-N-benzyloxymethyl-1-[(1S)-1-phenyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2,3-hexodiulofuranosyl]uracil

There total 2 articles about 3-N-benzyloxymethyl-1-[(1S)-1-phenyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2,3-hexodiulofuranosyl]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: 76.0%

: 100-52-7
benzaldehyde

: 476490-34-3
3-N-benzyloxymethyl-1-[1-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2-pentosulofuranosyl]uracil

: 3-N-benzyloxymethyl-1-[1-phenyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-erythro-2,3-hexodiulofuranosyl]uracil

: 476490-37-6
3-N-benzyloxymethyl-1-[(1S)-1-phenyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2,3-hexodiulofuranosyl]uracil

Guidance literature:: With samarium diiodide; oxygen; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/jo020266j

Reference yield:

: 288103-31-1
1-((2S,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-oxo-2-phenylselanyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione

: 476490-37-6
3-N-benzyloxymethyl-1-[(1S)-1-phenyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2,3-hexodiulofuranosyl]uracil

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / N,N-diisopropylethylamine / dimethylformamide / 0.33 h / 20 °C

2: 76 percent / SmI₂; O₂ / tetrahydrofuran / 1 h / -78 °C

With samarium diiodide; oxygen; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo020266j

Reference yield:

: 476490-37-6
3-N-benzyloxymethyl-1-[(1S)-1-phenyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2,3-hexodiulofuranosyl]uracil

: 476490-60-5
1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-2-((S)-hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / NaBH₄ / methanol / 0.5 h / 0 °C

2: 100 percent / H₂ / 10percent Pd/C / methanol / 40 h / 20 °C / atmospheric pressure

3: 74 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; 10percent Pd/C; In tetrahydrofuran; methanol;
DOI:10.1021/jo020266j