tert-butyl (2S,3R)-(3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-yl)[(4-methylphenyl)sulfenyl]carbamate

Base Information

• Chemical Name: tert-butyl (2S,3R)-(3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-yl)[(4-methylphenyl)sulfenyl]carbamate
• CAS No.: 955375-63-0
• Molecular Formula: C₂₂H₃₉NO₄SSi
• Molecular Weight: 441.707

Synonyms:tert-butyl (2S,3R)-(3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-yl)[(4-methylphenyl)sulfenyl]carbamate

Chemical Property of tert-butyl (2S,3R)-(3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-yl)[(4-methylphenyl)sulfenyl]carbamate

Chemical Property:

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Technology Process of tert-butyl (2S,3R)-(3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-yl)[(4-methylphenyl)sulfenyl]carbamate

There total 1 articles about tert-butyl (2S,3R)-(3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-yl)[(4-methylphenyl)sulfenyl]carbamate 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: 25.0%

tert-butyl (2S,3R,RS)-(3-(tert-butyldimethylsilyloxy)-4-[(4-methylphenyl)sulfinyl]butan-2-yl)carbamate → tert-butyl (2S,3R)-(3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-yl)[(4-methylphenyl)sulfenyl]carbamate (955375-63-0)

Guidance literature:

tert-butyl (2S,3R,R_S)-(3-(tert-butyldimethylsilyloxy)-4-[(4-methylphenyl)sulfinyl]butan-2-yl)carbamate; With 2,4,6-trimethyl-pyridine; trifluoroacetic anhydride; In acetonitrile; at 20 ℃; for 168h;

With sodium hydrogencarbonate; In acetonitrile; at 25 ℃; for 48h; Further stages.;

DOI:10.1016/j.tet.2007.07.072

Reference yield: 35.0%

tert-butyl (2S,3R)-(3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-yl)[(4-methylphenyl)sulfenyl]carbamate (955375-63-0) → tert-butyl (2S,3R)-(3-(tert-butyldimethylsilyloxy)-4-oxobutan-2-yl)[(4-methylphenyl)sulfenyl]carbamate

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 30h;

DOI:10.1016/j.tet.2007.07.072

Reference yield:

tert-butyl (2S,3R)-(3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-yl)[(4-methylphenyl)sulfenyl]carbamate (955375-63-0) → C22H37NO5SSi

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / pyridinium chlorochromate / CH₂Cl₂ / 30 h / 20 °C

2: aq. KMnO₄; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 0.17 h / 20 °C / pH 4

With potassium permanganate; sodium dihydrogenphosphate; pyridinium chlorochromate; In dichloromethane; tert-butyl alcohol;

DOI:10.1016/j.tet.2007.07.072

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