(2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Ss)-(toluene-4-sulfinyl)-pentane-2,3-diol

Base Information

• Chemical Name: (2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Ss)-(toluene-4-sulfinyl)-pentane-2,3-diol
• CAS No.: 1013326-19-6
• Molecular Formula: C₂₉H₃₇BrO₄SSi
• Molecular Weight: 589.666

Synonyms:(2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Ss)-(toluene-4-sulfinyl)-pentane-2,3-diol

Chemical Property of (2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Ss)-(toluene-4-sulfinyl)-pentane-2,3-diol

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Technology Process of (2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Ss)-(toluene-4-sulfinyl)-pentane-2,3-diol

There total 1 articles about (2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Ss)-(toluene-4-sulfinyl)-pentane-2,3-diol 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: 82.0%

(E)-(2S)-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Rs)-(toluene-4-sulfinyl)pent-3-en-2-ol (1013326-07-2) → (2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Ss)-(toluene-4-sulfinyl)-pentane-2,3-diol (1013326-19-6)

Guidance literature:

With N-Bromosuccinimide; water; In toluene; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2007.12.046

Reference yield: 90.0%

(2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Ss)-(toluene-4-sulfinyl)-pentane-2,3-diol (1013326-19-6) → (2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(toluene-4-sulfonyl)-pentane-2,3-diol (1013326-52-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2007.12.046

Reference yield: 76.0%

(2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Ss)-(toluene-4-sulfinyl)-pentane-2,3-diol (1013326-19-6) + 2,2-dimethoxy-propane (77-76-9) → {(R)-2-bromo-2-[(4S,5S)-2,2,4-trimethyl-5-(toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethoxy}-tert-butyldiphenylsilane (1013326-24-3)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2007.12.046

upstream raw materials:

(E)-(2S)-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(Rs)-(toluene-4-sulfinyl)pent-3-en-2-ol

Downstream raw materials:

(2S,3S,4R)-4-bromo-5-(tert-butyldiphenylsilanyloxy)-3-methyl-1-(toluene-4-sulfonyl)-pentane-2,3-diol

{(R)-2-bromo-2-[(4S,5S)-2,2,4-trimethyl-5-(toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethoxy}-tert-butyldiphenylsilane

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