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

Base Information

• Chemical Name: 5-O-(tert-butyldiphenylsilyl)-4-C-(hydroxymethyl)-1,2-O-isopropylidene-α-D-xylofuranose
• CAS No.: 861230-89-9
• Molecular Formula: C₂₅H₃₄O₆Si
• Molecular Weight: 458.627
• Mol file: 861230-89-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about 5-O-(tert-butyldiphenylsilyl)-4-C-(hydroxymethyl)-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: 93.0%

1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (55797-64-3,55797-65-4) + tert-butylchlorodiphenylsilane (58479-61-1) → 5-O-(tert-butyldiphenylsilyl)-4-C-(hydroxymethyl)-1,2-O-isopropylidene-α-D-xylofuranose (861230-89-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 36h;

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) → 5-O-(tert-butyldiphenylsilyl)-4-C-(hydroxymethyl)-1,2-O-isopropylidene-α-D-xylofuranose (861230-89-9)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1002/ejoc.200500023

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

upstream raw materials:

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

tert-butylchlorodiphenylsilane

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

Downstream raw materials:

4-C-(benzoyloxymethyl)-5-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