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

Base Information

• Chemical Name: 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
• CAS No.: 121846-02-4
• Molecular Formula: C₃₅H₃₈N₂O₁₂
• Molecular Weight: 678.693

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 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

There total 9 articles about 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 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:

2',3'-O-isopropylideneuridine (362-43-6) → 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 (121846-02-4,121865-33-6)

Guidance literature:

Multi-step reaction with 9 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

9: 1.) tin tetrachloride; 2.) 5percent HF-CH₃CN / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) 0 deg C, 10 min

With pyridine; lead(IV) acetate; osmium(VIII) oxide; boron trifluoride diethyl etherate; hydrogen fluoride; water; tin(IV) chloride; sodium hydride; sodium carbonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; acetonitrile; 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) → 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 (121846-02-4,121865-33-6)

Guidance literature:

Multi-step reaction with 8 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

8: 1.) tin tetrachloride; 2.) 5percent HF-CH₃CN / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) 0 deg C, 10 min

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

DOI:10.1021/ja00197a047

Reference yield:

(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 (121845-98-5) → 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 (121846-02-4,121865-33-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 67 percent / boron trifluoride etherate / various solvent(s) / 3 h / -78 °C

2: 96 percent / diisopropylethylamine / dimethylformamide / 3 h / Heating

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

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

5: 1.) tin tetrachloride; 2.) 5percent HF-CH₃CN / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) 0 deg C, 10 min

With lead(IV) acetate; osmium(VIII) oxide; boron trifluoride diethyl etherate; hydrogen fluoride; water; tin(IV) chloride; sodium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; acetonitrile; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00197a047

upstream raw materials:

1-benzoyloxy-2-tert-butyldimethylsilyloxy-4-methoxybuta-1,3-diene

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

2',3'-O-isopropylideneuridine

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

Downstream raw materials:

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

3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil

3-(4-Methoxybenzyl)-1-<(11R)-1,2,6-trideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-α-D-galacto-undecodialdo-1,5-pyrano<2,1-e><2-(benzyloxy)-4-(benzyloxycarbonyl)dihydro-Δ²-1,3,4-oxadiazinyl>-11,8-furanosyl>uracil

3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil

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