278750
(1R,2S,5R)-(−)-Menthyl (S)-p-toluenesulfinate
98%
Synonym(s):
(−)-(1R)-Menthyl (S)-p-toluenesulfinate, (S)-(−)-Menthyl p-toluenesulfinate
Assay
98%
form
solid
optical activity
[α]20/D −195°, c = 2 in acetone
mp
102-104 °C (lit.)
functional group
sulfinic acid
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
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
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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