(1R,4S,5R)-5-Acetoxy-4-acetylamino-1-{benzyloxy-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-cyclohex-2-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (1R,4S,5R)-5-Acetoxy-4-acetylamino-1-{benzyloxy-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-cyclohex-2-enecarboxylic acid methyl ester
• CAS No.: 286956-58-9
• Molecular Formula: C₃₄H₄₁N₄O₁₆P
• Molecular Weight: 792.69

Synonyms:(1R,4S,5R)-5-Acetoxy-4-acetylamino-1-{benzyloxy-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-cyclohex-2-enecarboxylic acid methyl ester

Chemical Property of (1R,4S,5R)-5-Acetoxy-4-acetylamino-1-{benzyloxy-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-cyclohex-2-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (1R,4S,5R)-5-Acetoxy-4-acetylamino-1-{benzyloxy-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-cyclohex-2-enecarboxylic acid methyl ester

There total 11 articles about (1R,4S,5R)-5-Acetoxy-4-acetylamino-1-{benzyloxy-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-cyclohex-2-enecarboxylic acid methyl 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:

(3aR,5R,7R,7aS)-5,7-Diacetoxy-2-oxo-hexahydro-2λ4-benzo[1,3,2]dioxathiole-5-carboxylic acid methyl ester → (1R,4S,5R)-5-Acetoxy-4-acetylamino-1-{benzyloxy-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-cyclohex-2-enecarboxylic acid methyl ester (286956-58-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 0.91 g / NaIO₄ / RuCl₃*H₂O / ethyl acetate; acetonitrile / 1 h / 0 - 20 °C

2: DBU / tetrahydrofuran / 0.5 h / 70 °C

3: 1.35 g / aq. H₂SO₄ / tetrahydrofuran / 1 h / 20 °C

4: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

5: 0.55 g / LiN₃ / dimethylformamide / 1 h / 70 °C

6: dithiothreitol / pyridine; H₂O / 1 h / 20 °C

7: 340 mg / pyridine / 15 h / 20 °C

8: 59 percent / NaOMe / methanol / 1 h / 20 °C

9: 62 percent / Pyridine; DMAP / ethyl acetate / 5 h / 20 °C

10: 120 mg / diisopropylethylamine / acetonitrile / 2.5 h / 20 °C

11: tetrazole / acetonitrile / 4 h / 20 °C

12: 62 mg / tBuOOH / acetonitrile / 1.5 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; dmap; sodium periodate; lithium azide; sulfuric acid; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; diothiothreitol; ruthenium trichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Oxidation / 2: Elimination / 3: Hydrolysis / 4: Acylation / 5: Substitution / 6: Reduction / 7: Acetylation / 8: Deacetylation / 9: Acetylation / 10: Condensation / 11: Condensation / 12: Oxidation;

DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

methyl (1R,4R,5R)-1,5-di-O-acetyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate (286956-49-8) → (1R,4S,5R)-5-Acetoxy-4-acetylamino-1-{benzyloxy-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-cyclohex-2-enecarboxylic acid methyl ester (286956-58-9)

Guidance literature:

Multi-step reaction with 9 steps

1: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

2: 0.55 g / LiN₃ / dimethylformamide / 1 h / 70 °C

3: dithiothreitol / pyridine; H₂O / 1 h / 20 °C

4: 340 mg / pyridine / 15 h / 20 °C

5: 59 percent / NaOMe / methanol / 1 h / 20 °C

6: 62 percent / Pyridine; DMAP / ethyl acetate / 5 h / 20 °C

7: 120 mg / diisopropylethylamine / acetonitrile / 2.5 h / 20 °C

8: tetrazole / acetonitrile / 4 h / 20 °C

9: 62 mg / tBuOOH / acetonitrile / 1.5 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; dmap; lithium azide; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; diothiothreitol; In pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Acylation / 2: Substitution / 3: Reduction / 4: Acetylation / 5: Deacetylation / 6: Acetylation / 7: Condensation / 8: Condensation / 9: Oxidation;

DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

(1R,4R,5R)-1,5-Diacetoxy-4-sulfooxy-cyclohex-2-enecarboxylic acid methyl ester → (1R,4S,5R)-5-Acetoxy-4-acetylamino-1-{benzyloxy-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-cyclohex-2-enecarboxylic acid methyl ester (286956-58-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.35 g / aq. H₂SO₄ / tetrahydrofuran / 1 h / 20 °C

2: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

3: 0.55 g / LiN₃ / dimethylformamide / 1 h / 70 °C

4: dithiothreitol / pyridine; H₂O / 1 h / 20 °C

5: 340 mg / pyridine / 15 h / 20 °C

6: 59 percent / NaOMe / methanol / 1 h / 20 °C

7: 62 percent / Pyridine; DMAP / ethyl acetate / 5 h / 20 °C

8: 120 mg / diisopropylethylamine / acetonitrile / 2.5 h / 20 °C

9: tetrazole / acetonitrile / 4 h / 20 °C

10: 62 mg / tBuOOH / acetonitrile / 1.5 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; dmap; lithium azide; sulfuric acid; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; diothiothreitol; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Hydrolysis / 2: Acylation / 3: Substitution / 4: Reduction / 5: Acetylation / 6: Deacetylation / 7: Acetylation / 8: Condensation / 9: Condensation / 10: Oxidation;

DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

upstream raw materials:

(benzyloxy)chloro(diisopropylamino)phosphane

methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-oxocyclohex-2-ene-1-carboxylate

methyl (1R,4R,5R)-1,5-di-O-acetyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate

methyl (1R,4S,5R)-1,5-di-O-acetyl-4-azido-1,5-dihydroxycyclohex-2-ene-1-carboxylate

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