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13730

Sigma-Aldrich

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

≥99.0% (sum of enantiomers, HPLC)

Synonym(s):

(2R,3S)-(+)-4-Benzyloxy-2,3-epoxy-1-butyl 4-nitrobenzoate

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About This Item

Empirical Formula (Hill Notation):
C18H17NO6
CAS Number:
Molecular Weight:
343.33
Beilstein:
5383515
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
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

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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

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