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CAS RN: 1264520-63-9 | Product Number: T2937

O-TBDPS-D-Thr-N-Boc-L-tert-Leu-Diphenylphosphine


Purity: >98.0%(HPLC)
Synonyms:
  • N-(tert-Butoxycarbonyl)-L-tert-leucine N-[(2R,3S)-3-(tert-Butyldiphenylsilyloxy)-1-(diphenylphosphino)-2-butyl]amide
  • N-Boc-L-tert-leucine N-[(2R,3S)-3-(tert-Butyldiphenylsilyloxy)-1-(diphenylphosphino)-2-butyl]amide
Documents:
100MG
£193.00
1   7  

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Product Number T2937
Purity / Analysis Method >98.0%(HPLC)
Molecular Formula / Molecular Weight C__4__3H__5__7N__2O__4PSi = 725.00  
Physical State (20 deg.C) Solid
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive
CAS RN 1264520-63-9
Reaxys Registry Number 21221495
PubChem Substance ID 172089008
Specifications
Appearance White to Almost white powder to crystal
Purity(HPLC) min. 98.0 area%
Elemental analysis(Nitrogen) 3.60 to 4.00 %
Specific rotation [a]20/D -26.0 to -29.0 deg(C=1、CHCl3)
Properties (reference)
Melting Point 56 °C
Specific Rotation -28° (C=1,CHCl3)
GHS
Related Laws:
Transport Information:
HS Number 2931499090
Application
A Novel Dipeptide-Based Chiral Phosphine Organocatalyst for Asymmetric Cyclization

Typical procedure (entry 1: R = CH3CH2CH2-): To a dried round bottom flask is added N-butylidene-P,P-diphenylphosphinic amide (27.1 mg, 0.1 mmol), O-TBDPS-D-Thr-N-Boc-L-tert-Leu-diphenylphosphine (3.6 mg, 0.005 mmol) and MS5Å (60 mg) under N2, followed by the addition of anhydrous Et2O (1 mL). The reaction mixture is cooled to 0 °C, tert-butyl 2,3-butadienoate (22 micro-L, 0.15 mmol) is then added, and the mixture is stirred at 0 °C for 30 min. The reaction mixture is then filtered (to remove MS5Å) and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent: hexane/EtOAc = 10:1 to 2:1) to afford the cycloaddition product (37.9 mg, 92% yield, 96% ee) as a colorless oil.

References


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