(2R,4S)-3-<(Benzyloxy)carbonyl>-4-(<(tert-butyloxy)carbonyl>enthyl)-4-methyl-2-phenyl-1,3-oxazolidin-5-one

Base Information

• Chemical Name: (2R,4S)-3-<(Benzyloxy)carbonyl>-4-(<(tert-butyloxy)carbonyl>enthyl)-4-methyl-2-phenyl-1,3-oxazolidin-5-one
• CAS No.: 135923-90-9
• Molecular Formula: C₂₅H₂₉NO₆
• Molecular Weight: 439.508

Synonyms:(2R,4S)-3-<(Benzyloxy)carbonyl>-4-(<(tert-butyloxy)carbonyl>enthyl)-4-methyl-2-phenyl-1,3-oxazolidin-5-one

Chemical Property of (2R,4S)-3-<(Benzyloxy)carbonyl>-4-(<(tert-butyloxy)carbonyl>enthyl)-4-methyl-2-phenyl-1,3-oxazolidin-5-one

Chemical Property:

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Technology Process of (2R,4S)-3-<(Benzyloxy)carbonyl>-4-(<(tert-butyloxy)carbonyl>enthyl)-4-methyl-2-phenyl-1,3-oxazolidin-5-one

There total 2 articles about (2R,4S)-3-<(Benzyloxy)carbonyl>-4-(<(tert-butyloxy)carbonyl>enthyl)-4-methyl-2-phenyl-1,3-oxazolidin-5-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: 63.0%

(2R,4S)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one (135923-86-3) → (2R,4S)-3-<(Benzyloxy)carbonyl>-4-(<(tert-butyloxy)carbonyl>enthyl)-4-methyl-2-phenyl-1,3-oxazolidin-5-one (135923-90-9)

Guidance literature:

(2R,4S)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

3-halide-propionic acid tert-butyl ester; In tetrahydrofuran; at -78 - 20 ℃; stereoselective reaction;

DOI:10.1021/jm800487r

Reference yield:

tert-Butyl acrylate (1663-39-4,25232-27-3) + (2R,4S)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one (135923-86-3) → (2R,4S)-3-<(Benzyloxy)carbonyl>-4-(<(tert-butyloxy)carbonyl>enthyl)-4-methyl-2-phenyl-1,3-oxazolidin-5-one (135923-90-9)

Guidance literature:

With n-butyllithium; diisopropylamine; Yield given. Multistep reaction; 1) THF, -78 deg C, 10 min., 2) a) -78 deg C, 3 h, b) r.t., overnight;

DOI:10.1002/hlca.19910740414

Reference yield:

(2R,4S)-3-<(Benzyloxy)carbonyl>-4-(<(tert-butyloxy)carbonyl>enthyl)-4-methyl-2-phenyl-1,3-oxazolidin-5-one (135923-90-9) → O5-(tert-Butyl) Hydrogen (R)-N2-<(Benzyloxy)carbonyl>-2-methylglutamate (135923-98-7)

Guidance literature:

With sodium hydroxide; water; In methanol; at 45 ℃;

DOI:10.1021/jm800487r

upstream raw materials:

tert-Butyl acrylate

(2R,4S)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one

Downstream raw materials:

O⁵-(tert-Butyl)-O¹-Methyl (S)-N²-<(Benzyloxy)carbonyl>-2-methylglutamate

O⁵-(tert-Butyl) Hydrogen (S)-N²-<(Benzyloxy)carbonyl>-2-methylglutamate

O⁵-(tert-Butyl) Hydrogen (R)-N²-<(Benzyloxy)carbonyl>-2-methylglutamate

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