(R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-hydroxypentanoyl)oxazolidin-2-one

Base Information

Chemical Name:(R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-hydroxypentanoyl)oxazolidin-2-one
CAS No.:866138-90-1
Molecular Formula:C₂₁H₃₃NO₅Si
Molecular Weight:407.582
Hs Code.:

Synonyms:(R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-hydroxypentanoyl)oxazolidin-2-one

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Chemical Property of (R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-hydroxypentanoyl)oxazolidin-2-one

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Technology Process of (R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-hydroxypentanoyl)oxazolidin-2-one

There total 12 articles about (R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-hydroxypentanoyl)oxazolidin-2-one 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: 93.0%

: 866138-77-4
(R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pentanoyl)oxazolidin-2-one

: 866138-90-1
(R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-hydroxypentanoyl)oxazolidin-2-one

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol051200o

Reference yield: 63.7%

: C₂₈H₃₉NO₅Si

: 866138-90-1
(R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-hydroxypentanoyl)oxazolidin-2-one

Guidance literature:: With palladium on activated charcoal; hydrogen; In ethyl acetate; under 3000.3 Torr;
DOI:10.1021/acs.joc.7b00228

Reference yield:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 866138-90-1
(R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-hydroxypentanoyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / NaH / dimethylformamide / 4 h / 20 °C

2: 100 percent / KOH / methanol / 6 h / Heating

3: imidazole / CH₂Cl₂ / 5 h / 20 °C

4: 6.6 g / aq. K₂CO₃ / methanol; tetrahydrofuran / 1 h / 0 °C

5: Et₃N / tetrahydrofuran / 3 h / 0 °C

6: 6.7 g / BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

7: 93 percent / DDQ; H₂O / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; potassium hydroxide; n-butyllithium; water; sodium hydride; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol051200o