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278750

Sigma-Aldrich

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

98%

Synonym(s):

(−)-(1R)-Menthyl (S)-p-toluenesulfinate, (S)-(−)-Menthyl p-toluenesulfinate

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About This Item

Empirical Formula (Hill Notation):
C17H26O2S
CAS Number:
1517-82-4
Molecular Weight:
294.45
Beilstein:
3207468
UNSPSC Code:
12352000
PubChem Substance ID:
24856828
NACRES:
NA.22

Assay

98%

form

solid

optical activity

[α]20/D −195°, c = 2 in acetone

mp

102-104 °C (lit.)

storage temp.

−20°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+/m1/s1

InChI key

NQICGNSARVCSGJ-ASKNOMKYSA-N

General description

(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate is mainly used for the introduction of p-toluenesulfinyl group in asymmetric synthesis.

Application

(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate can react with:
  • metal ketimines to form enantiopure sulfinimines
  • p-(methylthio)benzaldehyde to form (S)-(-)-N-(4-methylthiobenzylidene)-p-toluenesulfinimine

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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Asymmetric synthesis of the antibiotic (+)-thiamphenicol using cis-N-(p-toluenesulfinyl) aziridine 2-carboxylic acids
Davis FA and Zhou P.
Tetrahedron Letters, 35(41), 7525-7528 (1994)
Asymmetric synthesis and properties of sulfinimines (thiooxime S-oxides).
Davis FA, et al.
The Journal of Organic Chemistry, 62(8), 2555-2563 (1997)

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