(S)-3-Benzyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate

Base Information

• Chemical Name: (S)-3-Benzyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate
• CAS No.: 117833-99-5
• Molecular Formula: C15H19NO5
• Molecular Weight: 293.32
• DSSTox Substance ID: DTXSID601149324
• Nikkaji Number: J2.171.067I
• Mol file: 117833-99-5.mol

Synonyms:117833-99-5;(S)-3-BENZYL 4-METHYL 2,2-DIMETHYLOXAZOLIDINE-3,4-DICARBOXYLATE;(-)-(S)-3-Benzyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate;3-O-benzyl 4-O-methyl (4S)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate;DTXSID601149324;AT19386;BS-26449;2,2-Dimethyloxazolidine-3,4alpha-dicarboxylic acid 3-benzyl 4-methyl ester;3-BENZYL 4-METHYL (S)-2,2-DIMETHYLOXAZOLIDINE-3,4-DICARBOXYLATE;4-Methyl 3-(phenylmethyl) (4S)-2,2-dimethyl-3,4-oxazolidinedicarboxylate;3-BENZYL 4-METHYL (4S)-2,2-DIMETHYL-1,3-OXAZOLIDINE-3,4-DICARBOXYLATE

Chemical Property of (S)-3-Benzyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate

Chemical Property:

• Boiling Point: 128 - 130 °C (0.02 mmHg)
• PSA: 65.07000
• LogP: 1.87100
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 293.12632271
• Heavy Atom Count: 21
• Complexity: 390

Purity/Quality:

≥99% ^*data from raw suppliers

(-)-(S)-3-BENZYL 4-METHYL 2,2-DIMETHYLOXAZOLIDINE-3,4-DICARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(N(C(CO1)C(=O)OC)C(=O)OCC2=CC=CC=C2)C
• Isomeric SMILES: CC1(N([C@@H](CO1)C(=O)OC)C(=O)OCC2=CC=CC=C2)C

Technology Process of (S)-3-Benzyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate

There total 5 articles about (S)-3-Benzyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate 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: 100.0%

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) + 2,2-dimethoxy-propane (77-76-9) → N-benzyloxycarbonyl 4(S)-(1'-methoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine (117833-99-5)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 1h; Heating;

DOI:10.1016/S0040-4020(01)96112-5

Reference yield: 100.0%

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) → N-benzyloxycarbonyl 4(S)-(1'-methoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine (117833-99-5)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 12h;

DOI:10.1246/cl.2001.102

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → N-benzyloxycarbonyl 4(S)-(1'-methoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine (117833-99-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With potassium carbonate; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jo010456e

upstream raw materials:

L-serin

N-benzyloxycarbonyl-L-serine methyl ester

2,2-dimethoxy-propane

N-(benzyloxycarbonyl)-L-serine

Downstream raw materials:

(R)-4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

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

(4S)-N-benzyloxycarbonyl-4-carbamoyl-2,2-dimethyl-1,3-oxazolidine

(S)-2,2-dimethyl-4-methoxycarbonyl-1,3-oxazolidine