256277

Sigma-Aldrich

(R,R)-(+)-Hydrobenzoin

99%, optical purity ee: 99% (HPLC)

Synonym(s):
(R,R)-1,2-Diphenyl-1,2-ethanediol, (R,R)-1,2-Diphenylethylene glycol
Linear Formula:
C6H5CH(OH)CH(OH)C6H5
CAS Number:
Molecular Weight:
214.26
Beilstein/REAXYS Number:
2050815
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

99%

optical activity

[α]28/D +93°, c = 2.5 in ethanol

optical purity

ee: 99% (HPLC)

mp

146-149 °C (lit.)

SMILES string

O[C@@H]([C@H](O)c1ccccc1)c2ccccc2

InChI

1S/C14H14O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-16H/t13-,14-/m1/s1

InChI key

IHPDTPWNFBQHEB-ZIAGYGMSSA-N

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General description

(R,R)-(+)-Hydrobenzoin is a chiral 1,2-diol useful as a chiral reagent, building block, ligand or auxiliary in asymmetric synthesis.

Application

(R,R)-(+)-Hydrobenzoin may be used in the oxyselenenylation step in the multi-step synthesis of cyclopentitols and aminocyclopentitols from cyclopentene. It may also be used as a ligand for the asymmetric addition of diethylzinc to aldehydes in the presence or absence of titanium tetra-isopropoxide to form (R)- or (S)-form of the corresponding secondary alcohol, respectively.

Packaging

5, 25 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Synthesis of enantiopure cyclopentitols and aminocyclopentitols mediated by oxyselenenylation of cyclopentene with (R, R)-hydrobenzoin.
Kim KS, et al.
Tetrahedron Letters, 39(36), 6471-6474 (1998)
A practical stereoselective synthesis of chiral hydrobenzoins via asymmetric transfer hydrogenation of benzils.
Murata K, et al.
Organic Letters, 1(7), 1119-1121 (1999)
Divergent enantioselective pathways in the catalytic asymmetric addition of diethylzinc to aldehydes in the presence and absence of titanium tetraisopropoxide.
Dean MA and Hitchcock SR.
Tetrahedron Asymmetry, 19(22), 2563-2567 (2008)

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