(4S,2'S,3'R)-N⁽³⁾-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one

Base Information

• Chemical Name: (4S,2'S,3'R)-N⁽³⁾-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one
• CAS No.: 1190930-16-5
• Molecular Formula: C₂₀H₂₇NO₄
• Molecular Weight: 345.439

Synonyms:(4S,2'S,3'R)-N⁽³⁾-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one

Chemical Property of (4S,2'S,3'R)-N⁽³⁾-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one

Chemical Property:

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Technology Process of (4S,2'S,3'R)-N⁽³⁾-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one

There total 1 articles about (4S,2'S,3'R)-N⁽³⁾-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-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: 95.0%

(4S,2'E)-3-(but-2'-enoyl)-4-iso-propyl-5,5-dimethyloxazolidin-2-one (909731-28-8) + phenylacetaldehyde (122-78-1) → (4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one (1190930-16-5)

Guidance literature:

(4S,2'E)-3-(but-2'-enoyl)-4-iso-propyl-5,5-dimethyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 ℃; Inert atmosphere;

phenylacetaldehyde; In dichloromethane; at -78 - 20 ℃; for 1h; Inert atmosphere;

With water; dihydrogen peroxide; In methanol; dichloromethane; at 0 - 20 ℃; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2009.07.004

Reference yield: 96.0%

(4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one (1190930-16-5) + tert-butyldimethylsilyl chloride (18162-48-6) → (4S,2'S,3'R)-N(3)-[2'-vinyl-3'-(tert-butyldimethylsilyloxy)-4'-phenylbutanoyl]-4-isopropyl-5,5-dimethyl-oxazolidin-2-one (1190930-23-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tet.2009.07.004

Reference yield:

methanol (67-56-1) + (4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one (1190930-16-5) → methyl (2E,3R)-2-ethylidene-3-hydroxy-4-phenylbutanoate (1190930-39-2) + methyl (2Z,3R)-2-ethylidene-3-hydroxy-4-phenylbutanoate

Guidance literature:

methanol; (4S,2'S,3'R)-N⁽³⁾-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one; With n-butyllithium; at -78 - -20 ℃; Inert atmosphere;

With water; ammonium chloride; In methanol; pentane; Inert atmosphere;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at -20 ℃; for 36h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tet.2009.07.004

upstream raw materials:

(4S,2'E)-3-(but-2'-enoyl)-4-iso-propyl-5,5-dimethyloxazolidin-2-one

phenylacetaldehyde

Downstream raw materials:

methyl (2E,3R)-2-ethylidene-3-hydroxy-4-phenylbutanoate

C₁₃H₁₆O₃

(4S,2'S,3'R)-N⁽³⁾-[2'-vinyl-3'-(tert-butyldimethylsilyloxy)-4'-phenylbutanoyl]-4-isopropyl-5,5-dimethyl-oxazolidin-2-one

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