1,5-Anhydro-2-deoxy-4,6-O-[(R)-(4-methoxyphenyl)methylene]-3-O-[tris(1-methylethyl)silyl]-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,5-Anhydro-2-deoxy-4,6-O-[(R)-(4-methoxyphenyl)methylene]-3-O-[tris(1-methylethyl)silyl]-D-arabino-hex-1-enitol
• CAS No.: 187879-14-7
• Molecular Formula: C23H36O5Si
• Molecular Weight: 420.621

Synonyms:1,5-Anhydro-2-deoxy-4,6-O-[(R)-(4-methoxyphenyl)methylene]-3-O-[tris(1-methylethyl)silyl]-D-arabino-hex-1-enitol

Chemical Property of 1,5-Anhydro-2-deoxy-4,6-O-[(R)-(4-methoxyphenyl)methylene]-3-O-[tris(1-methylethyl)silyl]-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,5-Anhydro-2-deoxy-4,6-O-[(R)-(4-methoxyphenyl)methylene]-3-O-[tris(1-methylethyl)silyl]-D-arabino-hex-1-enitol

There total 3 articles about 1,5-Anhydro-2-deoxy-4,6-O-[(R)-(4-methoxyphenyl)methylene]-3-O-[tris(1-methylethyl)silyl]-D-arabino-hex-1-enitol 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: 95.0%

triisopropylsilyl chloride (13154-24-0) + 2,6-anhydro-5-deoxy-1,3-O-(4-methoxybenzylidene)-D-arabino-hex-5-enitol (187880-20-2) → 4,6-O-(4-methoxybenzylidene)-3-O-(triisopropyl)silyl-D-(-)-glucal (187879-14-7)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/jo034556r

Reference yield:

D-glucal (13265-84-4) → 4,6-O-(4-methoxybenzylidene)-3-O-(triisopropyl)silyl-D-(-)-glucal (187879-14-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / pyridinium p-toluenesulfonate / acetonitrile / 4.5 h / 0 - 20 °C

2: 95 percent / 4-dimethylaminopyridine; imidazole / dimethylformamide / 3 h / 20 °C

With 1H-imidazole; dmap; pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo034556r

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → 4,6-O-(4-methoxybenzylidene)-3-O-(triisopropyl)silyl-D-(-)-glucal (187879-14-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / pyridinium p-toluenesulfonate / acetonitrile / 4.5 h / 0 - 20 °C

2: 95 percent / 4-dimethylaminopyridine; imidazole / dimethylformamide / 3 h / 20 °C

With 1H-imidazole; dmap; pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo034556r

upstream raw materials:

triisopropylsilyl chloride

2,6-anhydro-5-deoxy-1,3-O-(4-methoxybenzylidene)-D-arabino-hex-5-enitol

p-Anisaldehyde dimethyl acetal

D-glucal

Downstream raw materials:

4,6-di-O-(4-methoxybenzyl)-2-deoxy-α,β-D-glucopyranose

2-deoxy-4,6-di-O-(4-methoxybenzyl)-D-gluco-γ-lactone

2-deoxy-1,3-dioxo-4,6-di-O-(4-methoxybenzyl)-D-(+)-glucopyranose

4,6-di-O-(4-methoxybenzyl)-3-O-(triisopropyl)silyl-D-(-)-glucal

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