5-Benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose

Base Information

• Chemical Name: 5-Benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose
• CAS No.: 153914-97-7
• Molecular Formula: C23H24O8
• Molecular Weight: 428.439
• Mol file: 153914-97-7.mol

Synonyms:5-Benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose

Chemical Property of 5-Benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose

Chemical Property:

• Melting Point: 148-150°C
• PSA: 100.52000
• LogP: 2.30790
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

99.90% ^*data from raw suppliers

5-Benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose

There total 8 articles about 5-Benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose 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%

5-O-Benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-β-L-threo-pentofuranose (230631-15-9) → 5-O-benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose (153914-97-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; at 50 ℃; for 72h;

Reference yield: 75.0%

benzoyl chloride (98-88-4) + 1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (55797-64-3,55797-65-4) → 5-O-benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose (153914-97-7)

Guidance literature:

With pyridine; In various solvent(s); at 0 ℃; for 1.5h;

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (350255-13-9) → 5-O-benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose (153914-97-7)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 25 °C / Inert atmosphere

2: acetic acid / water / 20 °C

3: sodium periodate / water; 1,4-dioxane / 0 - 20 °C

4: sodium hydroxide; water / tetrahydrofuran / 0 - 20 °C

5: pyridine / 0 - 20 °C / Inert atmosphere

6: hydrogen; palladium 10% on activated carbon; acetic acid / methanol / 72 h / 50 °C

With pyridine; sodium periodate; palladium 10% on activated carbon; water; hydrogen; sodium hydride; acetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;

upstream raw materials:

benzoyl chloride

1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose

Downstream raw materials:

3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

1-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)uracil

9-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)uracil

9-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)-N⁶-benzoyladenine

Refernces

• 1、 Surzhykov,Krayevsky. "Novel 4'-branched nucleosides". . p. 2283 - 2305. Retrieved 2007/10/02.
• 2、 Surzhikov, S. A.,Dyatkina, N. B.. "4'-BRANCHED NUCLEOSIDES. I. SYNTHESIS OF 3'-AMINO-4'-HYDROXYMETHYL-3'-DEOXYNUCLEOSIDES". . p. 408 - 413. Retrieved 2007/10/02.