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536652

Sigma-Aldrich

(S)-(−)-2-(Boc-amino)-1,4-butanediol

97%

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About This Item

Linear Formula:
HOCH2CH2CH[NHCO2C(CH3)3]CH2OH
CAS Number:
128427-10-1
Molecular Weight:
205.25
MDL number:
MFCD03093946
UNSPSC Code:
12352108
PubChem Substance ID:
24878173
NACRES:
NA.22

Quality Level

100

Assay

97%

optical activity

[α]20/D −8°, c = 1 in chloroform

mp

65-69 °C (lit.)

SMILES string

CC(C)(C)OC(=O)N[C@H](CO)CCO

InChI

1S/C9H19NO4/c1-9(2,3)14-8(13)10-7(6-12)4-5-11/h7,11-12H,4-6H2,1-3H3,(H,10,13)/t7-/m0/s1

InChI key

KLRRFBSWOIUAHZ-ZETCQYMHSA-N

Application

(S)-(−)-2-(Boc-amino)-1,4-butanediol can be used as a reactant to synthesize:
  • Thiourea-based organocatalysts for asymmetric Michael addition reactions of nitroalkenes to α-nitrocyclohexanone.
  • Bis-copper (II) complex based catalysts for enantioselective Michael reactions.

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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Asymmetric Michael additions of α-nitrocyclohexanone to aryl nitroalkenes catalyzed by natural amino acid-derived bifunctional thioureas
Jo?rres M, et al.
Organic Letters, 14(17), 4518-4521 (2012)
Copper (II) in organic synthesis. XI. Evaluation of the ligand architecture on the efficiency of a copper (II) catalyst for enantioselective Michael reactions
Desimoni G, et al.
Tetrahedron, 51(14), 4131-4144 (1995)

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