Tert-butyl (4S)-4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Base Information

• Chemical Name: Tert-butyl (4S)-4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS No.: 173065-16-2
• Molecular Formula: C12H19 N O3
• Molecular Weight: 225.288
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00457277
• Nikkaji Number: J1.288.836H
• Wikidata: Q72503142
• Mol file: 173065-16-2.mol

Synonyms:173065-16-2;(S)-2,2-Dimethyl-3-(N-Boc)-4-ethynyl-oxazolidine;(S)-2,2-DIMETHYL-3-BOC-4-ETHYNYLOXAZOLIDINE;Tert-butyl (4S)-4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate;(S)-tert-Butyl 4-ethynyl-2,2-dimethyloxazolidine-3-carboxylate;tert-Butyl (S)-4-ethynyl-2,2-dimethyloxazolidine-3-carboxylate;SCHEMBL1833725;DTXSID00457277;DPZQSYOKTUMHNY-VIFPVBQESA-N;YGA06516;MFCD16038238;AKOS015909107;AS-37820;CS-0088511;(S)-N-Boc-2,2-dimethyl-4-ethynyl-oxazolidine;A18307;(S)-tert-Butyl4-ethynyl-2,2-dimethyloxazolidine-3-carboxylate;(4S)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4beta-ethynyloxazolidine;(S)-4-ethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester;tert-Butyl (4S)4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Chemical Property of Tert-butyl (4S)-4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Chemical Property:

• Boiling Point: 277℃
• Flash Point: 121℃
• PSA: 38.77000
• Density: 1.06
• LogP: 1.92950
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 225.13649347
• Heavy Atom Count: 16
• Complexity: 332

Purity/Quality:

99% ^*data from raw suppliers

(S)-2,2-Dimethyl-3-boc-4-ethynyloxazolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Tert-butyl (4S)-4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

There total 7 articles about Tert-butyl (4S)-4-ethynyl-2,2-dimethyl-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: 98.0%

(S)-tert-butyl 4-(2,2-dibromovinyl)-2,2-dimethyloxazolidine-3-carboxylate (130418-98-3) → (4S)-4-ethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (173065-16-2)

Guidance literature:

With ethylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 0 ℃; for 2.33333h; Inert atmosphere;

DOI:10.1002/anie.201004963

Reference yield: 83.0%

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) + dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) → (4S)-4-ethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (173065-16-2)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c2cc17958j

Reference yield: 71.0%

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate (108149-60-6,95715-86-9) → (4S)-4-ethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (173065-16-2)

Guidance literature:

methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate; With diisobutylaluminium hydride; In n-heptane; dichloromethane; at -78 ℃;

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate; With potassium carbonate; In methanol; n-heptane; dichloromethane; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.05.139

upstream raw materials:

(S)-tert-butyl 4-(2,2-dibromovinyl)-2,2-dimethyloxazolidine-3-carboxylate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate

Downstream raw materials:

(S,Z)-tert-butyl 4-(2-isocyano-4-methoxystyryl)-2,2-dimethyloxazolidine-3-carboxylate

(S,Z)-tert-butyl 4-(2-formamido-4-methoxystyryl)-2,2-dimethyloxazolidine-3-carboxylate

(S,Z)-tert-butyl 4-(2-isocyanostyryl)-2,2-dimethyloxazolidine-3-carboxylate

(S,Z)-tert-butyl 4-(2-formamidostyryl)-2,2-dimethyloxazolidine-3-carboxylate

Refernces

• 1、 Yamada, Haruka,Hayashi, Takahiro,Usuki, Toyonobu. "Total synthesis of the COPD biomarker desmosine via stepwise Sonogashira cross-coupling reactions". . p. 673 - 683. Retrieved 2015/06/25.
• 2、 Yamakawa, Takayuki,Ideue, Eiji,Iwaki, Yuzo,Sato, Ayumu,Tokuyama, Hidetoshi,Shimokawa, Jun,Fukuyama, Tohru. "Total synthesis of tryprostatins A and B". experimental part. p. 6547 - 6560. Retrieved 2011/09/20.