BOC-D-Phenylglycinol

Base Information

• Chemical Name: BOC-D-Phenylglycinol
• CAS No.: 102089-74-7
• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.299
• Hs Code.: 29051990
• European Community (EC) Number: 600-273-1
• UNII: G846LR8HDC
• DSSTox Substance ID: DTXSID00426847
• Nikkaji Number: J756.440F
• Wikidata: Q72450289
• Mol file: 102089-74-7.mol

Synonyms:102089-74-7;BOC-D-Phenylglycinol;(R)-N-(tert-Butoxycarbonyl)-2-phenylglycinol;(-)-N-Boc-D-alpha-phenylglycinol;(R)-tert-butyl (2-hydroxy-1-phenylethyl)carbamate;N-Boc-D-2-phenylglycinol;(R)-2-(tert-Butoxycarbonylamino)-2-phenylethanol;n-boc-d-phenylglycinol;tert-butyl N-[(1R)-2-hydroxy-1-phenylethyl]carbamate;N-Boc-(R)-phenylglycinol;G846LR8HDC;tert-butyl [(1R)-2-hydroxy-1-phenylethyl]carbamate;Carbamic acid, [(1R)-2-hydroxy-1-phenylethyl]-, 1,1-dimethylethyl ester;Carbamic acid, N-[(1R)-2-hydroxy-1-phenylethyl]-, 1,1-dimethylethyl ester;(R)-(-)-2-(Boc-amino)-2-phenylethanol;(R)-1,1-Dimethylethyl (2-hydroxy-1-phenylethyl)carbamate;Boc-D-Phg-ol;MFCD00274205;Carbamic acid, (2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl ester, (R)-;N-Boc-R-Phenylglycinol;tert-Butyl ((1R)-2-hydroxy-1-phenylethyl)carbamate;(R)-2-((N-tert-Butoxycarbonyl)amino)-2-phenylethanol;(R)-2-[(N-tert-Butoxycarbonyl)amino]-2-phenylethanol;((R)-2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester;[(R)-2-hydroxy-1-phenyl-ethyl]-carbamic acid tert-butyl ester;Carbamic acid, ((1R)-2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl ester;Carbamic acid, N-((1R)-2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl ester;UNII-G846LR8HDC;N-Boc-alpha-D-phenylglycinol;tert-butyl (R)-(2-hydroxy-1-phenylethyl)carbamate;SCHEMBL127326;DTXSID00426847;IBDIOGYTZBKRGI-NSHDSACASA-N;(R)-2-(Boc-amino)-2-phenylethanol;(-)-N-Boc-D- alpha -phenylglycinol;AKOS016842291;AC-5649;AM90171;CS-W012848;(r)-N-boc-2-hydroxy-1-phenylethylamine;DS-11901;(-)-N-Boc-D-alpha-phenylglycinol, 99%;2(R)-t-butoxycarbonylamino-2-phenylethanol;N-(tert-Butoxycarbonyl)-D-2-phenylglycinol;2-(R)-t-Butoxycarbonylamino-2-phenylethanol;B3270;(2R)-2-t-Butoxycarbonylamino-2-phenylethanol;A22806;(R)-tert-butyl 2-hydroxy-1-phenylethylcarbamate;EN300-4346632;Q-101621;(betaR)-beta-(tert-Butoxycarbonylamino)benzeneethanol;((R)-2-Hydroxy-1-phenylethyl)carbamic acid tert-butyl ester

Chemical Property of BOC-D-Phenylglycinol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.4E-05mmHg at 25°C
• Melting Point: 137-139 °C(lit.)
• Refractive Index: 1.547
• Boiling Point: 382.4 °C at 760 mmHg
• PKA: 11.55±0.46(Predicted)
• Flash Point: 185 °C
• PSA: 58.56000
• Density: 1.102 g/cm³
• LogP: 2.63560
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 237.13649347
• Heavy Atom Count: 17
• Complexity: 242

Purity/Quality:

98% ^*data from raw suppliers

(-)-N-Boc-D-α-phenylglycinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-25-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CO)C1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CO)C1=CC=CC=C1
• Uses: Chiral building block

Technology Process of BOC-D-Phenylglycinol

There total 84 articles about BOC-D-Phenylglycinol 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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + D-2-phenylglycinol (56613-80-0) → (R)-N-(tert-butoxycarbonyl)phenylglycinol (67341-01-9,117049-14-6,138457-46-2,102089-74-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetasy.2007.11.003

Reference yield: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-azido-2-phenylethanol (124718-93-0) → tert-butyl 2-hydroxy-1-phenylethylcarbamate (102089-74-7,117049-14-6,138457-46-2,67341-01-9)

Guidance literature:

With sodium hydroxide; trimethylphosphane; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(01)00901-7

Reference yield: 98.0%

(4R,5S)-5-acetoxy-2-oxo-4-phenyloxazolidine-3-carboxylic acid tert-butylester (402741-11-1) → tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate (117049-14-6) + (R)-N-(tert-butoxycarbonyl)phenylglycinol (67341-01-9,117049-14-6,138457-46-2,102089-74-7)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -78 - -40 ℃;

DOI:10.1021/ja0174231

upstream raw materials:

styrene

N-chloro-N-sodio-tert-butylcarbamate

di-tert-butyl dicarbonate

2-azido-2-phenylethanol

Downstream raw materials:

(R)-tert-butyl N-<1-phenyl-2-<(p-toluenesulfonyl)oxy>ethyl>carbamate

2-Oxo-butyric acid (R)-2-tert-butoxycarbonylamino-2-phenyl-ethyl ester

tert-butyl (1R)-2-{[(1R,2S)-3-cyano-1-methyl-2-(phenylseleno)propyl]oxy}-1-phenylethylcarbamate

tert-butyl (1R)-2-{[(1S,2R)-3-cyano-1-methyl-2-(phenylseleno)propyl]oxy}-1-phenylethylcarbamate

Refernces

• 1、 Li, Jun,Yuan, Yong,Bao, Xiazhen,Sang, Tongzhi,Yang, Jie,Huo, Congde. "Visible-Light-Induced Intermolecular Oxyimination of Alkenes". . p. 3712 - 3717. Retrieved 2021.
• 2、 Agami, Claude,Couty, Francois,Hamon, Louis,Venier, Olivier. "Chiral oxazolidinones from N-Boc derivatives of β-amino alcohols. Effect of a N-methyl substituent on reactivity and stereoselectivity". . p. 4509 - 4512. Retrieved 1993.
• 3、 Marinzi, Chiara,Bark, Steven J.,Offer, John,Dawson, Philip E.. "A new scaffold for amide ligation". . p. 2323 - 2328. Retrieved 2001.
• 4、 Yadav,Reddy, B. V. Subba. "A mild and selective cleavage of p-methoxybenzyl Ethers by CBr4-MeOH". . p. 566 - 567. Retrieved 2000.
• 5、 Kantam, M. Lakshmi,Reddy, R. Sudarshan,Srinivas,Chakravarti,Sreedhar,Figueras,Venkat Reddy, Ch.. "Platinum nanoparticles supported on zirconia mediated synthesis of N-acyl and N-(tert-butoxycarbonyl)amines from nitroarenes and azides". . p. 96 - 101. Retrieved 2012.
• 6、 Heydari, Akbar,Shiroodi, Roohollah Kazem,Hamadi, Hossein,Esfandyari, Maryam,Pourayoubi, Mehrdad. "N-tert-Butoxycarbonylation of amines using H3PW12O40 as an efficient heterogeneous and recyclable catalyst". . p. 5865 - 5868. Retrieved 2007.
• 7、 Wata, Chisato,Hashimoto, Takuya. "Organoiodine-Catalyzed Enantioselective Intermolecular Oxyamination of Alkenes". supporting information. p. 1745 - 1751. Retrieved 2021/02/05.