ChemicalBook--->CAS DataBase List--->160885-98-3

160885-98-3

160885-98-3 Structure

160885-98-3 Structure
IdentificationMore
[Name]

FMOC-L-VALINOL
[CAS]

160885-98-3
[Synonyms]

FMOC-VAL-OL
160885-98-3
FMOC-VALINOL
Fmoc-L-Val-ol
FMOC-L-VALINOL
N-FMOC-L-VALINOL
N-Fmoc-L-valinol,98%
N-ALPHA-FMOC-L-VALINOL
REF DUPL: Fmoc-L-Val-OH
FMOC-L-VALINOL USP/EP/BP
Fmoc-L-valinol≥ 98% (HPLC)
FMOC-(S)-2-AMINO-3-METHYL-1-BUTANOL
N-FMOC-(S)-2-AMINO-3-METHYL-1-BUTANOL
(S)-2-(FMOC-AMINO)-3-METHYL-1-BUTANOL
N-(9-FLUORENYLMETHOXYCARBONYL)-L-VALINOL
NALPHA-9-Fluorenylmethoxycarbonyl-(S)-2-amino-3-methyl-1-butanol
(S)-(9H-fluoren-9-yl)methyl 1-hydroxy-3-methylbutan-2-ylcarbamate
N-(1-hydroxy-3-methylbutan-2-yl)carbamic acid 9H-fluoren-9-ylmethyl ester
(S)-2-(Fmoc-amino)-3-methyl-1-butanol, N-(9-Fluorenylmethoxycarbonyl)-L-valinol
CarbaMic acid,N-[(1S)-1-(hydroxyMethyl)-2-Methylpropyl]-, 9H-fluoren-9-ylMethyl ester
(S)-2-(9-Fluorenylmethyloxycarbonyl)amino-3-methyl-1-butanol, N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-valinol
[Molecular Formula]

C20H23NO3
[MDL Number]

MFCD00235961
[Molecular Weight]

325.4
[MOL File]

160885-98-3.mol
Chemical PropertiesBack Directory
[Melting point ]

129-133 °C(lit.)
[Boiling point ]

515.7±33.0 °C(Predicted)
[density ]

1.166±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
[form ]

Solid
[pka]

11.40±0.46(Predicted)
[Appearance]

White to off-white Solid
[Optical Rotation]

Consistent with structure
[CAS DataBase Reference]

160885-98-3(CAS DataBase Reference)
Safety DataBack Directory
[Safety Statements ]

S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
[WGK Germany ]

3
Hazard InformationBack Directory
[Chemical Properties]

White powder
[Uses]

FMOC-L-VALINOL is used as starting material for the synthesis of enantiopure β-amino acids. Used for the efficient synthesis of enantiopure tetrahydroisoquinoline compounds. An intermediate for the one-pot conversion of amino acid carbamate compounds into N-derived 2-azolidinone compounds.
[Synthesis]

FMOC-L-Valine

68858-20-8

FMOC-L-VALINOL

160885-98-3

GENERAL METHOD: To a tetrahydrofuran (THF, 10 mL) solution of Fmoc-L-valine (10 mmol) was added N,N-diisopropylethylamine (DIPEA, 11 mmol, 1.42 mL) and 50% propylphosphonic anhydride (T3P) in ethyl acetate (EtOAc) solution (20 mmol, 6.36 mL) at 0 °C, and the reaction was stirred mixture for about 10 minutes. Subsequently, an aqueous solution (0.3 mL) of sodium borohydride (NaBH4, 10 mmol, 388 mg) was slowly added to the reaction mixture at the same temperature and stirring was continued until the reaction was shown to be complete by thin layer chromatography (TLC). After completion of the reaction, the solvent was removed under reduced pressure by rotary evaporator and the crude product was extracted with ethyl acetate (EtOAc). The organic phase was washed sequentially with 5% aqueous citric acid (10 mL × 2), 5% aqueous sodium carbonate (Na2CO3) (10 mL × 2), water and saturated saline. Finally, the organic phase was dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to afford the target product (S)-(9H-fluoren-9-yl)methyl (1-hydroxy-3-methylbutan-2-yl)carbamate.

[References]

[1] Journal of Organic Chemistry, 2001, vol. 66, # 25, p. 8454 - 8462
[2] Tetrahedron Letters, 1999, vol. 40, # 23, p. 4395 - 4396
[3] Tetrahedron Letters, 2012, vol. 53, # 38, p. 5059 - 5063
[4] RSC Advances, 2014, vol. 4, # 87, p. 46947 - 46950
[5] Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4182 - 4187
Spectrum DetailBack Directory
[Spectrum Detail]

FMOC-L-VALINOL(160885-98-3)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

160885-98-3(sigmaaldrich)
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