(-)-(2R,3R,4R)-4-(t-Butyldimethylsiloxy)-2-(cyanomethyl)-tetrahydropyran-3-yl Benzoate

Base Information

• Chemical Name: (-)-(2R,3R,4R)-4-(t-Butyldimethylsiloxy)-2-(cyanomethyl)-tetrahydropyran-3-yl Benzoate
• CAS No.: 135123-07-8
• Molecular Formula: C₂₀H₂₉NO₄Si
• Molecular Weight: 375.54
• Mol file: 135123-07-8.mol

Synonyms:(-)-(2R,3R,4R)-4-(t-Butyldimethylsiloxy)-2-(cyanomethyl)-tetrahydropyran-3-yl Benzoate

Chemical Property of (-)-(2R,3R,4R)-4-(t-Butyldimethylsiloxy)-2-(cyanomethyl)-tetrahydropyran-3-yl Benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,3R,4R)-4-(t-Butyldimethylsiloxy)-2-(cyanomethyl)-tetrahydropyran-3-yl Benzoate

There total 9 articles about (-)-(2R,3R,4R)-4-(t-Butyldimethylsiloxy)-2-(cyanomethyl)-tetrahydropyran-3-yl Benzoate 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%

sodium cyanide (143-33-9,25596-52-5) + (-)-(2S,3R,4R)-2-Bromomethyl-4-(t-butyldimethylsilyloxy)-tetrahydropyran-3-yl Benzoate (131926-01-7) → (-)-(2R,3R,4R)-4-(t-Butyldimethylsiloxy)-2-(cyanomethyl)-tetrahydropyran-3-yl Benzoate (135123-07-8)

Guidance literature:

With sodium iodide; In dimethyl sulfoxide; at 80 ℃; for 5h;

Reference yield:

3,4,6-O-tri-O-acetyl-D-glucal (69534-73-2) → (-)-(2R,3R,4R)-4-(t-Butyldimethylsiloxy)-2-(cyanomethyl)-tetrahydropyran-3-yl Benzoate (135123-07-8)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / 5percent Pd-activated carbon / methanol / 4 h / Ambient temperature

2: NaOMe / methanol / 2 h / Ambient temperature

3: ZnCl₂ / 3 h / 80 °C

4: 97 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

5: 51 percent / NBS, azoisobutylnitrile / CCl₄ / 0.33 h / Heating; Irradiation

6: 95 percent / NaI / dimethylsulfoxide / 5 h / 80 °C

With 1H-imidazole; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); hydrogen; sodium methylate; sodium iodide; zinc(II) chloride; palladium on activated charcoal; In methanol; tetrachloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

(2S,3S,4R)-Tetrahydro-pyran-2,3,4-triol (20072-97-3,33428-78-3,75800-66-7,75800-68-9,78854-43-0,89919-60-8,126638-07-1,126638-08-2) → (-)-(2R,3R,4R)-4-(t-Butyldimethylsiloxy)-2-(cyanomethyl)-tetrahydropyran-3-yl Benzoate (135123-07-8)

Guidance literature:

Multi-step reaction with 4 steps

1: ZnCl₂ / 3 h / 80 °C

2: 97 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

3: 51 percent / NBS, azoisobutylnitrile / CCl₄ / 0.33 h / Heating; Irradiation

4: 95 percent / NaI / dimethylsulfoxide / 5 h / 80 °C

With 1H-imidazole; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium iodide; zinc(II) chloride; In tetrachloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

sodium cyanide

(-)-(2S,3R,4R)-2-Bromomethyl-4-(t-butyldimethylsilyloxy)-tetrahydropyran-3-yl Benzoate

(2S,3S,4R)-Tetrahydro-pyran-2,3,4-triol

3,4,6-O-tri-O-acetyl-D-glucal

Downstream raw materials:

(-)-O-(2R,3R,4R)-4-(t-Butyldimethylsiloxy)-2-(cyanomethyl)tetrahydropyran-2-yl O-Phenyl Thiocarbonate