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13730

Sigma-Aldrich

(2R,3S)-(+)-3-(Benzyloxymethyl)oxirane-2-methanol 4-nitrobenzoic acid ester

≥99.0% (sum of enantiomers, HPLC)

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Synonym(s):
(2R,3S)-(+)-4-Benzyloxy-2,3-epoxy-1-butyl 4-nitrobenzoate
Empirical Formula (Hill Notation):
C18H17NO6
CAS Number:
78469-86-0
Molecular Weight:
343.33
Beilstein:
5383515
MDL number:
MFCD00043126
UNSPSC Code:
12352005
PubChem Substance ID:
57647111
NACRES:
NA.22

Assay

≥99.0% (sum of enantiomers, HPLC)

form

solid

optical activity

[α]20/D +34±1°, c = 0.5% in chloroform

mp

78-80 °C

SMILES string

[O-][N+](=O)c1ccc(cc1)C(=O)OC[C@H]2O[C@H]2COCc3ccccc3

InChI

1S/C18H17NO6/c20-18(14-6-8-15(9-7-14)19(21)22)24-12-17-16(25-17)11-23-10-13-4-2-1-3-5-13/h1-9,16-17H,10-12H2/t16-,17+/m0/s1

InChI key

XBAOYRZETQXAAE-DLBZAZTESA-N

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Other Notes

Stable precursor to (2R,3S)-(+)-3-(benzyloxymethyl)oxirane-2-methanol which is a versatile chiral building block ; Nucleophilic substitution at carbon C-1 ; Cuprous iodide catalyzed addition of Grignard reagents at C-2

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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W.R. Roush et al.
Tetrahedron Letters, 24, 1377-1377 (1983)
C.H. Behrens et al.
The Journal of Organic Chemistry, 50, 5687-5687 (1985)
T. Katsuki et al.
The Journal of Organic Chemistry, 47, 1373-1373 (1982)

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