1-[1-azido-4,6-di-O-benzyl-3-O-methanesulfonyl-1-deoxy-β-D-fructofuranosyl]uracil

Base Information

Chemical Name:1-[1-azido-4,6-di-O-benzyl-3-O-methanesulfonyl-1-deoxy-β-D-fructofuranosyl]uracil
CAS No.:874812-53-0
Molecular Formula:C₂₅H₂₇N₅O₈S
Molecular Weight:557.584
Hs Code.:

Synonyms:1-[1-azido-4,6-di-O-benzyl-3-O-methanesulfonyl-1-deoxy-β-D-fructofuranosyl]uracil

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Chemical Property of 1-[1-azido-4,6-di-O-benzyl-3-O-methanesulfonyl-1-deoxy-β-D-fructofuranosyl]uracil

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Technology Process of 1-[1-azido-4,6-di-O-benzyl-3-O-methanesulfonyl-1-deoxy-β-D-fructofuranosyl]uracil

There total 9 articles about 1-[1-azido-4,6-di-O-benzyl-3-O-methanesulfonyl-1-deoxy-β-D-fructofuranosyl]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: 90.0%

: 874812-52-9
1-[1-azido-4,6-di-O-benzyl-1-deoxy-β-D-fructofuranosyl]uracil

: 124-63-0
methanesulfonyl chloride

: 874812-53-0
1-[1-azido-4,6-di-O-benzyl-3-O-methanesulfonyl-1-deoxy-β-D-fructofuranosyl]uracil

Guidance literature:: With pyridine; at 0 ℃; for 24h;
DOI:10.1021/jo052115x

Reference yield:

: 1-((2R,3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

: 874812-53-0
1-[1-azido-4,6-di-O-benzyl-3-O-methanesulfonyl-1-deoxy-β-D-fructofuranosyl]uracil

Guidance literature:: Multi-step reaction with 8 steps

1: 3.1 g / pyridine / 24 h / 20 °C

2: 91 percent / diphenyl carbonate; NaHCO₃ / dimethylformamide / 2 h / 110 °C

3: 85 percent / NaH / acetonitrile / 0 - 20 °C

4: 79 percent / aq. AcOH / 48 h / 20 °C

5: 89 percent / pyridine / 1.5 h / 0 °C

6: 87 percent / NaN₃ / dimethylformamide / 60 h / 100 °C

7: 85 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C

8: 90 percent / pyridine / 24 h / 0 °C

With pyridine; bis(phenyl) carbonate; sodium hydroxide; sodium azide; sodium hydride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo052115x

Reference yield:

: 874812-49-4
(2R,3R,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-9a-hydroxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one

: 874812-53-0
1-[1-azido-4,6-di-O-benzyl-3-O-methanesulfonyl-1-deoxy-β-D-fructofuranosyl]uracil

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / pyridine / 1.5 h / 0 °C

2: 87 percent / NaN₃ / dimethylformamide / 60 h / 100 °C

3: 85 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C

4: 90 percent / pyridine / 24 h / 0 °C

With pyridine; sodium hydroxide; sodium azide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;
DOI:10.1021/jo052115x