(S)-(-)-3-TERT-BUTOXYCARBONYL-4-FORMYL-2,2-DIMETHYL-1,3-OXAZOLIDINE

Base Information

• Chemical Name: (S)-(-)-3-TERT-BUTOXYCARBONYL-4-FORMYL-2,2-DIMETHYL-1,3-OXAZOLIDINE
• CAS No.: 102308-32-7
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.276
• Hs Code.: 29349990
• Mol file: 102308-32-7.mol

Synonyms:3-Oxazolidinecarboxylicacid, 4-formyl-2,2-dimethyl-, 1,1-dimethylethyl ester, (S)-;(-)-Garneraldehyde;(4S)-4-Formyl-2,2-dimethyl-3-oxazolidinecarboxylic acid1,1-dimethylethyl ester;(S)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-formyloxazolidine;(S)-4-Formyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester;(S)-Garner aldehyde;Garner's aldehyde;tert-Butyl(4S)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate;tert-Butyl (S)-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate;3-Oxazolidinecarboxylicacid, 4-formyl-2,2-dimethyl-, 1,1-dimethylethyl ester, (4S)-;

Chemical Property of (S)-(-)-3-TERT-BUTOXYCARBONYL-4-FORMYL-2,2-DIMETHYL-1,3-OXAZOLIDINE

Chemical Property:

• Appearance/Colour: Clear colorless to yellow oil
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Boiling Point: 302.738 °C at 760 mmHg
• PKA: -3.26±0.60(Predicted)
• Flash Point: 136.891 °C
• PSA: 55.84000
• Density: 1.129 g/cm³
• LogP: 1.49520
• Storage Temp.: 0-10°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water.

Purity/Quality:

98% ^*data from raw suppliers

(4S)-4-Formyl-2,2-dimethyl-3-oxazolidinecarboxylicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Chiral, non-racemic synthon for asymmetric synthesis of amino sugars and other nitrogen-containing targets. Widely utilized in the asymmetric synthesis of natural products.

Technology Process of (S)-(-)-3-TERT-BUTOXYCARBONYL-4-FORMYL-2,2-DIMETHYL-1,3-OXAZOLIDINE

There total 32 articles about (S)-(-)-3-TERT-BUTOXYCARBONYL-4-FORMYL-2,2-DIMETHYL-1,3-OXAZOLIDINE 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%

4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (108149-63-9) → (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1002/chem.200802337

Reference yield: 92.0%

(4S)-2,2-Dimethyl-4-(N-methoxy-N-methylcarbamoyl)oxazolidin-3-carbonsaeure-(tert-butyl)ester (122709-21-1,1822572-30-4) → (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2.33333h; Inert atmosphere; Cooling;

DOI:10.1002/adsc.201500794

Reference yield: 91.0%

3-tert-butyl 4-methyl 2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate (157604-46-1) → tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate (95715-87-0,102308-32-7,144070-30-4,127589-93-9)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 2.5h;

DOI:10.1016/j.ejmech.2005.03.024

upstream raw materials:

(S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester

4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

(4S)-2,2-Dimethyl-4-(N-methoxy-N-methylcarbamoyl)oxazolidin-3-carbonsaeure-(tert-butyl)ester

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

Downstream raw materials:

(S)-4-((R)-Hydroxy-phenyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(S)-tert-butyl 4-((S)-hydroxy(phenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

tert-butyl (4S)-4-<(1R)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

tert-butyl (4S)-4-<(1S)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Refernces

• 1、 Ocejo, Marta,Vicario, Jose L.,Badía, Dolores,Carrillo, Luisa,Reyes, Efraim. "A direct and efficient stereoconservative procedure for the selective oxidation of N-protected β-amino alcohols". . p. 2110 - 2112. Retrieved 2005.
• 2、 Roush,Hunt. "Asymmetric allylboration of 2-N,3-O-isopropylidene-N-Boc-L-serinal: Diastereoselective synthesis of the calicheamicin γ1(I) amino sugar". . p. 798 - 806. Retrieved 1995.
• 3、 Kahne, Daniel,Yang, Dan,Lee, May D.. "Preparation of the 4-Ethylamino Sugar of Calicheamicin: Assignment of Absolute Configuration". . p. 21 - 22. Retrieved 1990.
• 4、 Aglar, ?znur,Arenz, Christoph,Banhart, Sebastian,Cong, Xiaojing,Hamdo, Housam H.,Heuer, Dagmar,Kleuser, Burkhard,M?ller, Heiko M.,Saied, Essa M.,Samaha, Doaa,Schumacher, Fabian. "Liposomal FRET Assay Identifies Potent Drug-Like Inhibitors of the Ceramide Transport Protein (CERT)". . p. 16616 - 16621. Retrieved 2020.
• 5、 Shimada, Naoyuki,Ohse, Naoki,Takahashi, Naoya,Urata, Sari,Koshizuka, Masayoshi,Makino, Kazuishi. "Direct Synthesis of N -Protected Serine- And Threonine-Derived Weinreb Amides via Diboronic Acid Anhydride-Catalyzed Dehydrative Amidation: Application to the Concise Synthesis of -Garner's Aldehyde". . p. 1024 - 1028. Retrieved 2021.
• 6、 Belanger, Dominique,Tong, Xia,Soumare, Sadia,Dory, Yves L.,Zhao, Yue. "Cyclic peptide-polymer complexes and their self-assembly". . p. 4428 - 4436. Retrieved 2009.
• 7、 Hryniewicka, Agnieszka,?otowski, Zenon,Seroka, Barbara,Witkowski, Stanis?aw,Morzycki, Jacek W.. "Synthesis of a cisplatin derivative from lithocholic acid". . p. 5392 - 5398. Retrieved 2018.
• 8、 McKillop,Taylor,Watson,Lewis. "An improved procedure for the preparation of the Garner aldehyde and its use for the synthesis of N-protected 1-halo-2-(R)-amino-3-butenes". . p. 31 - 33. Retrieved 1994.
• 9、 Trajkovic, Milos,Ferjancic, Zorana,Saicic, Radomir N.. "A convenient procedure for the preparation of Garner's aldehyde". . p. 602 - 604. Retrieved 2012.