1-(6-Deoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-β-D-allo-heptadialdo-1,4-furanosyl)-3-(4-methoxybenzyl)uracil

Base Information

• Chemical Name: 1-(6-Deoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-β-D-allo-heptadialdo-1,4-furanosyl)-3-(4-methoxybenzyl)uracil
• CAS No.: 121846-01-3
• Molecular Formula: C₂₄H₃₀N₂O₉
• Molecular Weight: 490.51

Synonyms:1-(6-Deoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-β-D-allo-heptadialdo-1,4-furanosyl)-3-(4-methoxybenzyl)uracil

Chemical Property of 1-(6-Deoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-β-D-allo-heptadialdo-1,4-furanosyl)-3-(4-methoxybenzyl)uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(6-Deoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-β-D-allo-heptadialdo-1,4-furanosyl)-3-(4-methoxybenzyl)uracil

There total 8 articles about 1-(6-Deoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-β-D-allo-heptadialdo-1,4-furanosyl)-3-(4-methoxybenzyl)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:

1-[(3aR,4R,6R,6aR)-6-((R)-3,4-Dihydroxy-1-methoxymethoxy-butyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-(4-methoxy-benzyl)-1H-pyrimidine-2,4-dione → 1-(6-Deoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-β-D-allo-heptadialdo-1,4-furanosyl)-3-(4-methoxybenzyl)uracil (121846-01-3)

Guidance literature:

With lead(IV) acetate; sodium carbonate; In dichloromethane; at 0 ℃; for 0.0833333h; Yield given;

DOI:10.1021/ja00197a047

Reference yield:

2',3'-O-isopropylideneuridine (362-43-6) → 1-(6-Deoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-β-D-allo-heptadialdo-1,4-furanosyl)-3-(4-methoxybenzyl)uracil (121846-01-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / triethylamine / CH₂Cl₂ / 0.08 h / Ambient temperature

2: NaH / dimethylformamide / 0.17 h / 0 °C

3: K₂CO₃ / methanol / 2 h / Ambient temperature

4: 79 percent / dimethyl sulfoxide, trifluoroacetic acid, pyridine, dicyclohexylcarbodiimide / benzene / 6 h / 5 °C

5: 67 percent / boron trifluoride etherate / various solvent(s) / 3 h / -78 °C

6: 96 percent / diisopropylethylamine / dimethylformamide / 3 h / Heating

7: osmium tetroxide, 4-methylmorpholine N-oxide, H₂O / tetrahydrofuran / 4 h / Ambient temperature

8: lead tetraacetate, sodium carbonate / CH₂Cl₂ / 0.08 h / 0 °C

With pyridine; lead(IV) acetate; osmium(VIII) oxide; boron trifluoride diethyl etherate; water; sodium hydride; sodium carbonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00197a047

Reference yield:

1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil (15922-23-3) → 1-(6-Deoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-β-D-allo-heptadialdo-1,4-furanosyl)-3-(4-methoxybenzyl)uracil (121846-01-3)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / dimethylformamide / 0.17 h / 0 °C

2: K₂CO₃ / methanol / 2 h / Ambient temperature

3: 79 percent / dimethyl sulfoxide, trifluoroacetic acid, pyridine, dicyclohexylcarbodiimide / benzene / 6 h / 5 °C

4: 67 percent / boron trifluoride etherate / various solvent(s) / 3 h / -78 °C

5: 96 percent / diisopropylethylamine / dimethylformamide / 3 h / Heating

6: osmium tetroxide, 4-methylmorpholine N-oxide, H₂O / tetrahydrofuran / 4 h / Ambient temperature

7: lead tetraacetate, sodium carbonate / CH₂Cl₂ / 0.08 h / 0 °C

With pyridine; lead(IV) acetate; osmium(VIII) oxide; boron trifluoride diethyl etherate; water; sodium hydride; sodium carbonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00197a047

upstream raw materials:

2',3'-O-isopropylideneuridine

1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil

(3aR,4S,6R,6aS)-6-(3-(4-methoxybenzyl)-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxole-4-carbaldehyde

1-(6,7,8-Trideoxy-2,3-O-isopropylidene-β-D-allo-oct-7-enofuranosyl)-3-(4-methoxybenzyl)uracil

Downstream raw materials:

Benzoic acid 2-((R)-2-{(3aR,4R,6R,6aR)-6-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-methoxymethoxy-ethyl)-4-oxo-3,4-dihydro-2H-pyran-3-yl ester

1-(7,11-Anhydro-6,10-dideoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-D-arabino-β-D-allo-undec-10-enofuranosyl)-3-(4-methoxybenzyl)uracil

1-(7,11-Anhydro-6,10-dideoxy-2,3:8,9-di-O-isopropylidene-5-O-(methoxymethyl)-D-arabino-β-D-allo-undec-10-enofuranosyl)-3-(4-methoxybenzyl)uracil

3-(4-Methoxymethyl)-1-uracil

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