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  • 901233 - (2R)-2-Phenyl-3,4-dihydro-2H-pyrimido[2,1-b][1,3]benzothiazole

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901233 Sigma-Aldrich

(2R)-2-Phenyl-3,4-dihydro-2H-pyrimido[2,1-b][1,3]benzothiazole

≥95%

Synonym: (R)-2-Phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine, (R)-Homobenzotetramisole, Birman (R)-HBTM

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Kinetic Resolution
Quality Level   100
assay   ≥95%
form   powder or chunks
mp   145-147 °C
storage temp.   2-8°C
SMILES string   C12=CC=CC=C1SC3=N[C@@H](C4=CC=CC=C4)CCN23
InChI   1S/C16H14N2S/c1-2-6-12(7-3-1)13-10-11-18-14-8-4-5-9-15(14)19-16(18)17-13/h1-9,13H,10-11H2/t13-/m1/s1
InChI key   ZMYZJAQMQBHNLH-CYBMUJFWSA-N

Description

Application

This chiral isothiourea homobenzotetramisole ((R)-HBTM) developed by the Birman lab is an organocatalyst that has been used for kinetic resolution, determination of absolute configuration, and nucleophile-catalysed, Michael–aldol-b-lactonization (NCMAL). This same product was previously listed as L511730, and the complementary (S)-HBTM organocatalyst (900542) is also available.

Other Notes


Technology Spotlight: Homobenzotetramisole (HBTM): A General Organocatalyst for Asymmetric Acylations

[1] Determination of the Absolute Configuration β-Chiral Primary Alcohols Using the Competing Enantioselective Conversion Method

[2] Asymmetric Catalytic Synthesis of Thiochromenes via an Acyl Transfer-Initiated Cascade

[3] Rapid assembly of complex cyclopentanes employing chiral, α, β-unsaturated acylammonium intermediates

[4] Determination of Absolute Configuration Using Kinetic Resolution Catalysts

[5] Kinetic Resolution of Secondary Alcohols Using Amidine-Based Catalysts

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

Related Products

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Product #

Description

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900542 (2S)-2-Phenyl-3,4-dihydro-2H-pyrimido[2,1-b][1,3]benzothiazole, 95%
RNI00145 (2S)-2-Phenyl-2,3-dihydroimidazo[2,1-b][1,3]benzothiazole

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