4-C-(benzoyloxymethyl)-5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose

Base Information

• Chemical Name: 4-C-(benzoyloxymethyl)-5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose
• CAS No.: 861230-90-2
• Molecular Formula: C₃₂H₃₈O₇Si
• Molecular Weight: 562.735

Synonyms:4-C-(benzoyloxymethyl)-5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose

Chemical Property of 4-C-(benzoyloxymethyl)-5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of 4-C-(benzoyloxymethyl)-5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose

There total 3 articles about 4-C-(benzoyloxymethyl)-5-O-(tert-butyldiphenylsilyl)-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: 86.0%

5-O-(tert-butyldiphenylsilyl)-4-C-(hydroxymethyl)-1,2-O-isopropylidene-α-D-xylofuranose (861230-89-9) + benzoyl chloride (98-88-4) → 4-C-(benzoyloxymethyl)-5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose (861230-90-2)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1002/ejoc.200500023

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (72261-44-0) → 4-C-(benzoyloxymethyl)-5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose (861230-90-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / ammonium formate / Pd(OH)2/C / methanol / 16 h / Heating

2: 93 percent / triethylamine / CH₂Cl₂ / 36 h / 20 °C

3: 86 percent / pyridine / CH₂Cl₂ / 12 h / 0 - 20 °C

With pyridine; ammonium formate; triethylamine; palladium dihydroxide; In methanol; dichloromethane;

DOI:10.1002/ejoc.200500023

Reference yield:

1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (55797-64-3,55797-65-4) → 4-C-(benzoyloxymethyl)-5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose (861230-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / triethylamine / CH₂Cl₂ / 36 h / 20 °C

2: 86 percent / pyridine / CH₂Cl₂ / 12 h / 0 - 20 °C

With pyridine; triethylamine; In dichloromethane;

DOI:10.1002/ejoc.200500023

upstream raw materials:

5-O-(tert-butyldiphenylsilyl)-4-C-(hydroxymethyl)-1,2-O-isopropylidene-α-D-xylofuranose

benzoyl chloride

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

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

Downstream raw materials:

4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose

1-[2-O-acetyl-4-C-(benzoyloxymethyl)-β-D-xylofuranosyl]thymine

3,5-di-O-benzoyl-1,2-O-isopropylidene-4-C-(N-methylpiperazinyl)methyl-α-D-xylofuranose

1,2-di-O-acetyl-3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-α,β-D-xylofuranose

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