3-<(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)methyl>-5-methoxycarbonyl-4-hydroxypyrazole

Base Information

• Chemical Name: 3-<(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)methyl>-5-methoxycarbonyl-4-hydroxypyrazole
• CAS No.: 73556-58-8
• Molecular Formula: C₃₃H₃₄N₂O₇
• Molecular Weight: 570.642
• Mol file: 73556-58-8.mol

Synonyms:3-<(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)methyl>-5-methoxycarbonyl-4-hydroxypyrazole

Chemical Property of 3-<(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)methyl>-5-methoxycarbonyl-4-hydroxypyrazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-<(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)methyl>-5-methoxycarbonyl-4-hydroxypyrazole

There total 11 articles about 3-<(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)methyl>-5-methoxycarbonyl-4-hydroxypyrazole 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: 37.0%

methanol (67-56-1) + 2-(ethoxycarbonylmethyl-hydrazono)-O5,O6-isopropylidene-O8-trityl-D-allo-4,7-anhydro-2,3-dideoxy-octonic acid methyl ester (73556-57-7) → 3-<(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)methyl>-5-methoxycarbonyl-4-hydroxypyrazole (73556-58-8)

Guidance literature:

With sodium methylate; for 4.5h; Heating;

DOI:10.1246/bcsj.56.2700

Reference yield:

methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptanoate (56752-57-9) → 3-<(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)methyl>-5-methoxycarbonyl-4-hydroxypyrazole (73556-58-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 83 percent / LiAlH₄ / tetrahydrofuran / 1.33 h / -20 - 20 °C

2: 63 percent / pyridine / 15 h / 0 °C

3: 67 percent / perhydrodibenzo-18-crown-6 / acetonitrile / 15 h / Heating

4: KOH / ethane-1,2-diol / 20 h / 120 °C

5: diethyl ether; ethyl acetate

6: 1.) lithium diisopropylamide / 1.) hexane, THF, -78 deg C, 30 min, 2.) hexane, THF, from -78 deg C, 30 min to 0 deg C, 4 h

7: dimethylformamide / 12 h / 20 °C

8: 1. O₃, 2.) Me₂S / 1.) ethyl acetate, -78 deg C, 2.) ethyl acetate, from -78 deg C to 25 deg C, 3 h

9: AcONa / methanol; tetrahydrofuran; H₂O / 12 h / 25 °C

10: 37 percent / MeONa / 4.5 h / Heating

With pyridine; perhydrodibenzo-18-crown-6; potassium hydroxide; lithium aluminium tetrahydride; dimethylsulfide; sodium methylate; sodium acetate; ozone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; water; ethylene glycol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/bcsj.56.2700

Reference yield:

2-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)ethanol (73485-68-4) → 3-<(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)methyl>-5-methoxycarbonyl-4-hydroxypyrazole (73556-58-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 63 percent / pyridine / 15 h / 0 °C

2: 67 percent / perhydrodibenzo-18-crown-6 / acetonitrile / 15 h / Heating

3: KOH / ethane-1,2-diol / 20 h / 120 °C

4: diethyl ether; ethyl acetate

5: 1.) lithium diisopropylamide / 1.) hexane, THF, -78 deg C, 30 min, 2.) hexane, THF, from -78 deg C, 30 min to 0 deg C, 4 h

6: dimethylformamide / 12 h / 20 °C

7: 1. O₃, 2.) Me₂S / 1.) ethyl acetate, -78 deg C, 2.) ethyl acetate, from -78 deg C to 25 deg C, 3 h

8: AcONa / methanol; tetrahydrofuran; H₂O / 12 h / 25 °C

9: 37 percent / MeONa / 4.5 h / Heating

With pyridine; perhydrodibenzo-18-crown-6; potassium hydroxide; dimethylsulfide; sodium methylate; sodium acetate; ozone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; water; ethylene glycol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/bcsj.56.2700

upstream raw materials:

2-(ethoxycarbonylmethyl-hydrazono)-O⁵,O⁶-isopropylidene-O⁸-trityl-D-allo-4,7-anhydro-2,3-dideoxy-octonic acid methyl ester

sodium methylate

methanol

methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptanoate

Downstream raw materials:

3-<(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)methyl>-5-carbamoyl-4-hydroxypyrazole