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668370

Sigma-Aldrich

(S,S)-(+)-2,6-Bis[2-(hydroxydiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenol

95%

Synonym(s):

(S,S)-2,6-Bis[2-(hydroxydiphenylmethyl)pyrrolidin-1-ylmethyl]-4-methylphenol, Trost (S,S)-Bis-ProPhenol Ligand

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About This Item

Empirical Formula (Hill Notation):
C43H46N2O3
Molecular Weight:
638.84
MDL number:
MFCD08276890
UNSPSC Code:
12352005
PubChem Substance ID:
24884980
NACRES:
NA.22

assay

95%

form

solid

optical activity

[α]/D +50°, c = 1 in chloroform

impurities

≤6% dichloromethane and/or diethylether

mp

93-102 °C

functional group

hydroxyl
phenyl

SMILES string

Cc1cc(CN2CCC[C@H]2C(O)(c3ccccc3)c4ccccc4)c(O)c(CN5CCC[C@H]5C(O)(c6ccccc6)c7ccccc7)c1

InChI

1S/C43H46N2O3/c1-32-28-33(30-44-26-14-24-39(44)42(47,35-16-6-2-7-17-35)36-18-8-3-9-19-36)41(46)34(29-32)31-45-27-15-25-40(45)43(48,37-20-10-4-11-21-37)38-22-12-5-13-23-38/h2-13,16-23,28-29,39-40,46-48H,14-15,24-27,30-31H2,1H3/t39-,40-/m0/s1

InChI key

NEOVWBNAXIBNRT-ZAQUEYBZSA-N

Application

A useful catalyst in asymmetric aldol, Henry, and Mannich-type reactions.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2

supp_hazards

EUH019

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000302028
0000215234
0000194081
BGBC1470V
99597KJ

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Barry M Trost et al.
Journal of the American Chemical Society, 127(11), 3666-3667 (2005-03-18)
Direct asymmetric aldol reactions constitute a powerful methodology for the efficient synthesis of complex natural products. Herein we report the first application of our recently reported dinuclear Zn-catalyzed direct aldol addition of alkynyl ketones to aldehydes in a short and

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