(R)-3-tert-Butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate

Base Information

• Chemical Name: (R)-3-tert-Butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate
• CAS No.: 95715-86-9
• Molecular Formula: C₁₂H₂₁NO₅
• Molecular Weight: 259.302
• Hs Code.: 29349990
• European Community (EC) Number: 625-916-3
• DSSTox Substance ID: DTXSID60350836
• Nikkaji Number: J1.410.237J
• Wikidata: Q82126934
• Mol file: 95715-86-9.mol

Synonyms:95715-86-9;(R)-3-tert-Butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate;Methyl (R)-(+)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate;Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate;3-O-tert-butyl 4-O-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate;Methyl (R)-(+)-3-Boc-2,2-dimethyl-4-oxazolidinecarboxylate;MFCD00674041;(R)-(+)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylic Acid Methyl Ester;(R)-(-)-3-BOC-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine;3-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate;SCHEMBL121419;(R)-Methyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate;DTXSID60350836;CS-D1220;AKOS015893990;PS-7373;AM804613;BP-12795;B5352;EN300-651263;A846907;Methyl(R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate;(R)-(+)-3-Boc-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine;Methyl (R)-(+)-3-Boc-2,2-dimethyl-4-oxazolidinecarboxylate, 98%;3-tert-Butyl 4-Methyl (R)-(+)-2,2-Dimethyloxazolidine-3,4-dicarboxylate;Methyl 3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-(R)-carboxylate;O3-tert-Butyl O4-methyl (4R)-2,2-dimethyloxazolidine-3,4-dicarboxylate;(4R)-2,2-Dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl 4-methyl ester;(R)-(+)-2,2-Dimethyloxazolidine-3,4-dicarboxylic Acid 3-tert-Butyl 4-Methyl Ester;(R)-(+)-3-(tert-Butoxycarbonyl)-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine;(R)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester;3,4-Oxazolidinedicarboxylicacid,2,2-dimethyl-,3-(1,1-dimethylethyl)4-methyl ester,(4R)-;3-(1,1-Dimethylethyl)-4-methyl-(R)-2,2-dimethyl-3,4-oxazolidine carboxylate;3-(1,1-Dimethylethyl)-4-methyl-(r)-2,2-dimethyl-3,4-oxazolidinedicarboxylate

Chemical Property of (R)-3-tert-Butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate

Chemical Property:

• Appearance/Colour: liquid
• Vapor Pressure: 0.000629mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Boiling Point: 309.7 °C at 760mmHg
• PKA: -3.58±0.60(Predicted)
• Flash Point: 141.1 °C
• PSA: 65.07000
• Density: 1.107 g/cm³
• LogP: 1.46930
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 259.14197277
• Heavy Atom Count: 18
• Complexity: 345

Purity/Quality:

99.3% ^*data from raw suppliers

(R)-(+)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(N(C(CO1)C(=O)OC)C(=O)OC(C)(C)C)C
• Isomeric SMILES: CC1(N([C@H](CO1)C(=O)OC)C(=O)OC(C)(C)C)C
• Uses: Intermediate in the preparation of various enzymatic inhibitors.

Technology Process of (R)-3-tert-Butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate

There total 23 articles about (R)-3-tert-Butyl 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%

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8) + 2,2-dimethoxy-propane (77-76-9) → methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate (108149-60-6,95715-86-9)

Guidance literature:

With boron trifluoride diethyl etherate; In acetone;

DOI:10.1016/j.bmcl.2007.12.047

Reference yield: 99.0%

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) + 2,2-dimethoxy-propane (77-76-9) → (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester (95715-86-9,108149-60-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 25 ℃; for 3h; Automated synthesizer;

DOI:10.3762/bjoc.13.13

Reference yield: 93.0%

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) + 2,2-dimethoxy-propane (77-76-9) → methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate (108149-60-6,95715-86-9)

Guidance literature:

boron trifluoride diethyl etherate; In acetone; for 12h; Ambient temperature;

DOI:10.1246/cl.1987.2085

upstream raw materials:

N-tert-butyloxycarbonyl-L-serine methyl ester

2,2-dimethoxy-propane

diazomethane

(S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid

Downstream raw materials:

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

(S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid

tert-butyl (3E,1R,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-carbamate

[2-(3-formylphenoxy)-1-(hydroxymethyl)ethyl]carbamic acid tert-butyl ester

Refernces

• 1、 Yu, Hai,Gadi, Madhusudhan Reddy,Bai, Yuanyuan,Zhang, Libo,Li, Lei,Yin, Jun,Wang, Peng G.,Chen, Xi. "Chemoenzymatic Total Synthesis of GM3 Gangliosides Containing Different Sialic Acid Forms and Various Fatty Acyl Chains". . p. 8672 - 8682. Retrieved 2021/07/20.
• 2、 Mallik,Prasad,Das,Sen. "Alcohol functionality in the fatty acid backbone of sphingomyelin guides the inhibition of blood coagulation". . p. 3390 - 3398. Retrieved 2021/02/03.