Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester
• CAS No.: 114861-44-8
• Molecular Formula: C₁₉H₂₈O₅Si
• Molecular Weight: 364.514
• Mol file: 114861-44-8.mol

Synonyms:Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester

Chemical Property of Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester

There total 6 articles about Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester 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: 77.0%

6-O-tert-butyldimethylsilyl-D-glucal (58871-09-3) + benzoyl chloride (98-88-4) → (-)-(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3-hydroxy-4-(benzoyloxy)-3,4-dihydro-2H-pyran (114861-44-8,124648-31-3)

Guidance literature:

With pyridine; dmap; at -35 - 25 ℃; for 12h;

DOI:10.1021/jo00248a010

Reference yield:

D-glucal (13265-84-4) → (-)-(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3-hydroxy-4-(benzoyloxy)-3,4-dihydro-2H-pyran (114861-44-8,124648-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / imidazole / dimethylformamide / 12 h / 25 °C

2: 77 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / -35 - 25 °C

With pyridine; 1H-imidazole; dmap; In N,N-dimethyl-formamide;

DOI:10.1021/jo00248a010

Reference yield:

D-glucal triacetate (2873-29-2) → (-)-(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3-hydroxy-4-(benzoyloxy)-3,4-dihydro-2H-pyran (114861-44-8,124648-31-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / sodium methoxide / methanol / 3 h / 25 °C

2: 94 percent / imidazole / dimethylformamide / 12 h / 25 °C

3: 77 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / -35 - 25 °C

With pyridine; 1H-imidazole; dmap; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00248a010

upstream raw materials:

6-O-tert-butyldimethylsilyl-D-glucal

benzoyl chloride

tert-butyldimethylsilyl chloride

D-glucal

Downstream raw materials:

4-O-benzyl-6-O-tert-butyldimethylsilyl-D-(-)-glucal

1,5-anhydro-3-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol

1,5-anhydro-3-O-benzoyl-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol

C₁₉H₂₉NO₇SSi