(S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 108149-65-1
• Molecular Formula: C₁₁H₂₁NO₄
• Molecular Weight: 231.292
• Hs Code.: 2934999090
• European Community (EC) Number: 802-260-8
• DSSTox Substance ID: DTXSID40453495
• Nikkaji Number: J889.102H
• Wikidata: Q82274645
• Mol file: 108149-65-1.mol

Synonyms:108149-65-1;(S)-tert-butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate;(S)-1-Boc-2,2-Dimethyl-4-hydroxymethyl-oxazolidine;(S)-4-HYDROXYMETHYL-2,2-DIMETHYL-OXAZOLIDINE-3-CARBOXYLIC ACID TERT-BUTYL ESTER;tert-Butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate;tert-butyl (S)-4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate;(S)-tert-butyl4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate;SCHEMBL1526136;AMY4612;DTXSID40453495;DWFOEHLGMZJBAA-QMMMGPOBSA-N;MFCD11041410;AKOS015909330;AS-36335;B5657;CS-0130855;EN300-651262;(4S)-2,2-Dimethyl-3-(tert-butoxycarbonyl)oxazolidine-4beta-methanol;(S)-4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 36 °C
• Refractive Index: 1.464
• Boiling Point: 314.07°C at 760 mmHg
• PKA: 14.54±0.10(Predicted)
• Flash Point: 143.745°C
• PSA: 59.00000
• Density: 1.076g/cm³
• LogP: 1.28860
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 231.14705815
• Heavy Atom Count: 16
• Complexity: 270

Purity/Quality:

97% ^*data from raw suppliers

(S)-1-Boc-2,2-dimethyl-4-hydroxymethyl-oxazolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 26 articles about (S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 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%

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (108149-63-9,108149-65-1)

Guidance literature:

With zirconium(IV) tetraisopropoxide 2-propanol; 1,1'-bi-2-naphthol; In toluene; at 20 ℃; for 4h;

DOI:10.1016/S0040-4039(01)01276-X

Reference yield: 99.0%

methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate (108149-60-6,95715-86-9) → tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (108149-63-9,108149-65-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 25 ℃; for 0.666667h;

DOI:10.1002/jccs.201100637

Reference yield: 98.0%

(R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (198417-70-8) → tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (108149-63-9,108149-65-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1055/s-1997-3186

upstream raw materials:

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

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

3-tert-butyl 4-methyl 2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

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

Downstream raw materials:

(S)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (4R)-2,2-dimethyl-3-[(1,1-dimethylethoxy)carbonyl]-4-hydroxymethyloxazolidine ester

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4R)-2,2-dimethyl-4-[1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosylmethyl)-1H-tetrazol-5-yloxymethyl]oxazolidine-3-carboxylic acid tert-butyl ester

(4R)-2,2-dimethyl-4-[1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosylmethyl)-1H-tetrazol-5-yloxymethyl]oxazolidine-3-carboxylic acid tert-butyl ester