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438960

Sigma-Aldrich

(R)-(+)-3-Benzyloxy-1,2-propanediol

99%

Synonym(s):

(R)-Glycerol 1-benzyl ether, 3-O-Benzyl-sn-glycerol, 3-Benzyl-sn-glycerol

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About This Item

Linear Formula:
C6H5CH2OCH2CH(OH)CH2OH
CAS Number:
56552-80-8
Molecular Weight:
182.22
Beilstein:
2048922
MDL number:
MFCD00067260
UNSPSC Code:
12352201
PubChem Substance ID:
24867485
NACRES:
NA.22

Assay

99%

form

solid

optical activity

[α]20/D +5.5°, c = 20 in chloroform

mp

25-29 °C (lit.)

storage temp.

2-8°C

SMILES string

OC[C@@H](O)COCc1ccccc1

InChI

1S/C10H14O3/c11-6-10(12)8-13-7-9-4-2-1-3-5-9/h1-5,10-12H,6-8H2/t10-/m1/s1

InChI key

LWCIBYRXSHRIAP-SNVBAGLBSA-N

Application

Employed in the synthesis of a cyclopropyl chiron used in the preparation of 2,3-methanoamino acids. Chiral building block in the synthesis of petrosynes and biologically important phospholipid analogs.

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)

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Iguchi, K. et al.
The Journal of Organic Chemistry, 58, 5690-5690 (1993)
Burgess, K. et al.
The Journal of Organic Chemistry, 58, 3767-3767 (1993)
S.F. Martin et al.
The Journal of Organic Chemistry, 59, 4805-4805 (1994)
T N Wheeler et al.
Journal of medicinal chemistry, 37(24), 4118-4129 (1994-11-25)
The substrate specificity at the active site of recombinant human synovial fluid phospholipase A2 (hs-PLA2) was investigated by the preparation of a series of short-chain phospholipid analogs and measurement of their enzymatic hydrolysis at concentrations well below the critical micelle

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