3-O-(TERT-BUTYLDIMETHYLSILYL)-4,6-O-(4-METHOXYBENZYLIDENE)-D-GLUCAL

Base Information

• Chemical Name: 3-O-(TERT-BUTYLDIMETHYLSILYL)-4,6-O-(4-METHOXYBENZYLIDENE)-D-GLUCAL
• CAS No.: 384346-91-2
• Molecular Formula: C20H30O5Si
• Molecular Weight: 378.541
• Mol file: 384346-91-2.mol

Synonyms:3-O-(TERT-BUTYLDIMETHYLSILYL)-4,6-O-(4-METHOXYBENZYLIDENE)-D-GLUCAL;1,5-Anhydro-2-deoxy-3-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-[(4-methoxyphenyl)methylene]-D-arabino-hex-1-enitol

Chemical Property of 3-O-(TERT-BUTYLDIMETHYLSILYL)-4,6-O-(4-METHOXYBENZYLIDENE)-D-GLUCAL

Chemical Property:

• Melting Point: −30 °C(lit.)
• Boiling Point: 445.3±45.0 °C(Predicted)
• PSA: 57.15000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 4.67600
• Storage Temp.: -20°C

Purity/Quality:

95% ^*data from raw suppliers

3-O-TERT-BUTYLDIMETHYLSILYL-4,6-O-(4-METHOXYBENZYLIDENE)-D-GLUCAL 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-O-(TERT-BUTYLDIMETHYLSILYL)-4,6-O-(4-METHOXYBENZYLIDENE)-D-GLUCAL

There total 3 articles about 3-O-(TERT-BUTYLDIMETHYLSILYL)-4,6-O-(4-METHOXYBENZYLIDENE)-D-GLUCAL 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: 91.0%

(4aR,8R,8aS)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol (312623-79-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 3-O-tert-butyldimethylsilyl-4,6-O-(4-methoxybenzylidene)-D-(-)-glucal (384346-91-2)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 23 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03228

Reference yield:

D-glucal (13265-84-4) → 3-O-tert-butyldimethylsilyl-4,6-O-(4-methoxybenzylidene)-D-(-)-glucal (384346-91-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / tetrahydrofuran / 2 h / 23 °C / Inert atmosphere

2: dmap; 1H-imidazole / N,N-dimethyl-formamide / 12 h / 23 °C / Inert atmosphere

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

DOI:10.1021/acs.orglett.8b03228

Reference yield:

D-glucal triacetate (2873-29-2) → 3-O-tert-butyldimethylsilyl-4,6-O-(4-methoxybenzylidene)-D-(-)-glucal (384346-91-2)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol; potassium carbonate / 5 h / 23 °C / Inert atmosphere

2: pyridinium p-toluenesulfonate / tetrahydrofuran / 2 h / 23 °C / Inert atmosphere

3: dmap; 1H-imidazole / N,N-dimethyl-formamide / 12 h / 23 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; pyridinium p-toluenesulfonate; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.8b03228

upstream raw materials:

(4aR,8R,8aS)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol

tert-butyldimethylsilyl chloride

D-glucal

D-glucal triacetate

Downstream raw materials:

((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol

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