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282367

Sigma-Aldrich

(1S,2S,3R,5S)-(+)-Pinanediol

99%

Synonym(s):

(+)-2-Hydroxyisopinocampheol, (1S,2S,3R,5S)-2,3-Pinanediol, (1S,2S,3R,5S)-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol, [1S-(1α,2α,3α,5α)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol

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About This Item

Empirical Formula (Hill Notation):
C10H18O2
CAS Number:
18680-27-8
Molecular Weight:
170.25
Beilstein:
1853591
MDL number:
MFCD00077851
UNSPSC Code:
12352001
PubChem Substance ID:
24857043
NACRES:
NA.22

Assay

99%

form

solid

optical activity

[α]20/D +8.5°, c = 6.5 in toluene

optical purity

ee: 99% (GLC)

mp

57-59 °C (lit.)

SMILES string

CC1(C)C2C[C@@H](O)[C@@](C)(O)C1C2

InChI

1S/C10H18O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,11-12H,4-5H2,1-3H3/t6-,7-,8+,10-/m0/s1

InChI key

MOILFCKRQFQVFS-OORONAJNSA-N

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Application

(1S,2S,3R,5S)-(+)-Pinanediol can be used as a chiral reagent in the synthesis of homochiral α-hydroxyketones and in the resolution of prolineboronate esters.

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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Organic letters, 9(21), 4315-4318 (2007-09-18)
syn-beta-Hydroxyallylsilanes of general structure 11 and 28 are prepared in 50-86% yield and 91-95% ee (for aliphatic aldehydes; 50% ee for benzaldehyde) via the BF(3).Et(2)O-promoted gamma-silylallylboration reactions, using reagents 14 and 15.
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