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361887

Sigma-Aldrich

(1S,2S)-(+)-Thiomicamine

99%

Synonym(s):

(1S,2S)-(+)-2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol

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About This Item

Linear Formula:
4-(CH3S)C6H4CH(OH)CH(NH2)CH2OH
CAS Number:
16854-32-3
Molecular Weight:
213.30
EC Number:
240-878-4
MDL number:
MFCD00134212
UNSPSC Code:
12352112
PubChem Substance ID:
24862274
NACRES:
NA.22

Assay

99%

optical activity

[α]25/D +25°, c = 1 in ethanol

mp

151-154 °C (lit.)

SMILES string

CSc1ccc(cc1)[C@H](O)[C@@H](N)CO

InChI

1S/C10H15NO2S/c1-14-8-4-2-7(3-5-8)10(13)9(11)6-12/h2-5,9-10,12-13H,6,11H2,1H3/t9-,10-/m0/s1

InChI key

IULJJGJXIGQINK-UWVGGRQHSA-N

Application

(1S,2S)-(+)-Thiomicamine can be used:
  • As a starting material in the synthesis of 3,4-dihydroisoquinolinium salts, which are employed as promoters in asymmetric epoxidation and oxidation reactions.[1]
  • As a starting material in the synthesis of an α-amino acid named (3R,4R)-4-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, which is used to prepare modified peptides of biological importance.[2]
  • As a chiral base in the resolution of an angiotensin II type 2 receptor [AT2R] antagonist named EMA401.[3]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
S34065
35791
05904EI
02113BX
34860

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Transformation of (+)-thiomicamine into chiral non-racemic 3, 4-dihydroisoquinolinium salts: application for catalytic asymmetric epoxidation of alkenes and oxidation of sulfides
Gluszynska A, et al.
Tetrahedron Asymmetry, 15(16), 2499-2505 (2004)
Stereoselective synthesis of 3-mono-and 1, 3-disubstituted 4-phenyl-1, 2, 3, 4-tetrahydroisoquinolines
Brozda D, et al.
Tetrahedron Asymmetry, 11(14), 3017-3025 (2000)
Synthesis of enantiopure angiotensin II type 2 receptor [AT2R] antagonist EMA401
Wakchaure PB, et al.
Tetrahedron, 71(38), 6881-6887 (2015)

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