Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-tetrahydro-pyran-3-yl ester
• CAS No.: 194590-99-3
• Molecular Formula: C₂₁H₃₃BrO₅Si
• Molecular Weight: 473.48
• Mol file: 194590-99-3.mol

Synonyms:Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-tetrahydro-pyran-3-yl ester

There total 4 articles about Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-tetrahydro-pyran-3-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:

[(2R,3S,4R)-3,4-bis(acetyloxy)-6-hydroxyoxan-2-yl]methyl acetate (17326-97-5,115655-96-4,135824-44-1,135824-45-2) → Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-tetrahydro-pyran-3-yl ester (194590-99-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / imidazole / CH₂Cl₂

2: NaOMe / methanol / -20 °C

3: 77 percent / pyridinium toluenesulfonate

4: 72 percent / N-bromosuccinimide, BaCO₃ / CCl₄

With 1H-imidazole; N-Bromosuccinimide; sodium methylate; pyridinium p-toluenesulfonate; barium carbonate; In methanol; tetrachloromethane; dichloromethane;

DOI:10.1016/S0040-4039(97)01224-0

Reference yield:

(2R,3S,4R,6S)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol (194590-98-2) → Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-tetrahydro-pyran-3-yl ester (194590-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / pyridinium toluenesulfonate

2: 72 percent / N-bromosuccinimide, BaCO₃ / CCl₄

With N-Bromosuccinimide; pyridinium p-toluenesulfonate; barium carbonate; In tetrachloromethane;

DOI:10.1016/S0040-4039(97)01224-0

Reference yield:

Acetic acid (2R,3S,4R,6S)-3-acetoxy-2-acetoxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-tetrahydro-pyran-4-yl ester (194590-97-1) → Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-tetrahydro-pyran-3-yl ester (194590-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol / -20 °C

2: 77 percent / pyridinium toluenesulfonate

3: 72 percent / N-bromosuccinimide, BaCO₃ / CCl₄

With N-Bromosuccinimide; sodium methylate; pyridinium p-toluenesulfonate; barium carbonate; In methanol; tetrachloromethane;

DOI:10.1016/S0040-4039(97)01224-0

upstream raw materials:

[(2R,3S,4R)-3,4-bis(acetyloxy)-6-hydroxyoxan-2-yl]methyl acetate

(2R,3S,4R,6S)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Acetic acid (2R,3S,4R,6S)-3-acetoxy-2-acetoxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-tetrahydro-pyran-4-yl ester

D-glucal triacetate