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278742

Sigma-Aldrich

(1S,2R,5S)-(+)-Menthyl (R)-p-toluenesulfinate

98%

Synonym(s):

(R)-(+)-Menthyl p-toluenesulfinate

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About This Item

Empirical Formula (Hill Notation):
C17H26O2S
CAS Number:
91796-57-5
Molecular Weight:
294.45
UNSPSC Code:
12352000
PubChem Substance ID:
24856827
NACRES:
NA.22

Assay

98%

form

solid

optical activity

[α]20/D +200°, c = 2 in acetone

mp

104-106 °C (lit.)

storage temp.

2-8°C

SMILES string

C[C@H]1CC[C@H](C(C)C)[C@H](C1)OS(=O)c2ccc(C)cc2

InChI

1S/C17H26O2S/c1-12(2)16-10-7-14(4)11-17(16)19-20(18)15-8-5-13(3)6-9-15/h5-6,8-9,12,14,16-17H,7,10-11H2,1-4H3/t14-,16+,17-,20+/m0/s1

InChI key

NQICGNSARVCSGJ-DZIWXPPMSA-N

Application

(1S,2R,5S)-(+)-Menthyl (R)-p-toluenesulfinate can be used:
  • As a chiral electrophile in the synthesis of fluorescent triazolopyridine ligands.
  • To prepare various sulfinimines, which are further used in the synthesis of α-aminophosphonic acids by reacting with borane complexes.
  • In one of the key synthetic steps for the synthesis of (S)-(+)-ethyl β-amino-3-pyridinepropanoate, a component of an antiplatelet agent.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Triazolopyridines. Part 25: Synthesis of new chiral ligands from [1, 2, 3] triazolo [1, 5-a] pyridines
Abarca B, et al.
Tetrahedron, 63(42), 10479-10485 (2007)
A new efficient procedure for asymmetric synthesis of alpha-aminophosphonic acids via addition of lithiated bis (diethylamino) phosphine borane complex to enantiopure sulfinimines
Mikolajczyk M, et al.
Tetrahedron Asymmetry, 13(23), 2571-2576 (2002)
An Efficient Synthesis of (S)-(+)-Ethyl beta-Amino-3-pyridinepropanoate Using Enantiopure Sulfinimines
Davis FA, et al.
The Journal of Organic Chemistry, 61(6), 2222-2225 (1996)

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