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254827

Sigma-Aldrich

(+)-Noe-lactol™ dimer

≥99%

Synonym(s):

(+)-MBF-OH dimer, (+)-Noe’s reagent, (2R,3aS,4R,7aS)-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl ether, Bis[(2R,3aS,4R,7aS)octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl] ether

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About This Item

Empirical Formula (Hill Notation):
C24H38O3
CAS Number:
87248-50-8
Molecular Weight:
374.56
MDL number:
MFCD00074783
UNSPSC Code:
12352005
PubChem Substance ID:
24855268
NACRES:
NA.22

Assay

≥99%

form

solid

optical activity

[α]21/D +199.1°, c = 2.25 in THF

mp

150-151 °C (lit.)

SMILES string

CC1(C)[C@@H]2CC[C@@]1(C)[C@H]3O[C@@H](C[C@@H]23)O[C@@H]4C[C@H]5[C@H]6CC[C@@](C)([C@H]5O4)C6(C)C

InChI

1S/C24H38O3/c1-21(2)15-7-9-23(21,5)19-13(15)11-17(26-19)25-18-12-14-16-8-10-24(6,20(14)27-18)22(16,3)4/h13-20H,7-12H2,1-6H3/t13-,14-,15+,16+,17-,18-,19-,20-,23-,24-/m0/s1

InChI key

VUDXCBLBKXFCNA-VFQSMPPFSA-N

Application

(+)-Noe-lactol™ dimer can be used to prepare:
  • Axially chiral isoquinoline derivatives by reacting with pyridinium p-toluenesulfonate.
  • Halofuginone lactate.

Legal Information

Noe-Lactol is a trademark of Sigma-Aldrich Co. LLC

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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(2R, 3S)-(+)-and (2S, 3R)-(−)-Halofuginone lactate: Synthesis, absolute configuration, and activity against Cryptosporidium parvum
Linder MR, et al.
Bioorganic & medicinal chemistry letters, 17(15), 4140-4143 (2007)
Enantioselective synthesis of axially chiral 1-(1-naphthyl) isoquinolines and 2-(1-naphthyl) pyridines through sulfoxide ligand coupling reactions
Baker RW, et al.
Tetrahedron, 61(15), 3733-3743 (2005)

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