benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino)butyl-1,3-oxazolidine-3-carboxylate

Base Information

• Chemical Name: benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino)butyl-1,3-oxazolidine-3-carboxylate
• CAS No.: 239789-45-8
• Molecular Formula: C₂₁H₃₃N₃O₅
• Molecular Weight: 407.51
• Mol file: 239789-45-8.mol

Synonyms:benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino)butyl-1,3-oxazolidine-3-carboxylate

Chemical Property of benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino)butyl-1,3-oxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino)butyl-1,3-oxazolidine-3-carboxylate

There total 6 articles about benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino)butyl-1,3-oxazolidine-3-carboxylate 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: 50.0%

N-BOC-1,2-diaminoethane (57260-73-8) + (4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde (117833-92-8) → benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino)butyl-1,3-oxazolidine-3-carboxylate (239789-45-8)

Guidance literature:

With sodium cyanoborohydride; In methanol; acetic acid;

DOI:10.1016/S0040-4039(99)00909-0

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino)butyl-1,3-oxazolidine-3-carboxylate (239789-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / triethylamine / CHCl₃ / 4 h

2: 35 percent / sodium cyanoborohydride; acetic acid / methanol

With sodium cyanoborohydride; acetic acid; triethylamine; In methanol; chloroform;

DOI:10.1021/jo010456e

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino)butyl-1,3-oxazolidine-3-carboxylate (239789-45-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / potassium carbonate / dimethylformamide / 4 h / 20 °C

2: 81 percent / TsOH monohydrate / 3 h / Heating

3: 58 percent / DIBALH / toluene / 3 h / -78 °C

4: 35 percent / sodium cyanoborohydride; acetic acid / methanol

With diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; In methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo010456e

upstream raw materials:

N-BOC-1,2-diaminoethane

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

di-tert-butyl dicarbonate

N-(benzyloxycarbonyl)-L-serine

Downstream raw materials:

benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino-2-propionyl)butyl-1,3-oxazolidine-3-carboxylate

(R)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-propionyl-4-azalysinol