359068
(−)-Dimethyl 2,3-O-isopropylidene-L-tartrate
97%
Synonym(s):
(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester, Dimethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
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About This Item
Empirical Formula (Hill Notation):
C9H14O6
CAS Number:
Molecular Weight:
218.20
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
15406
Assay:
97%
Form:
liquid
assay
97%
form
liquid
optical activity
[α]20/D −54°, neat
refractive index
n20/D 1.439 (lit.)
bp
150 °C/19 mmHg (lit.)
density
1.190 g/mL at 20 °C (lit.)
functional group
ester, ether, ketal
SMILES string
COC(=O)[C@@H]1OC(C)(C)O[C@H]1C(=O)OC
InChI
1S/C9H14O6/c1-9(2)14-5(7(10)12-3)6(15-9)8(11)13-4/h5-6H,1-4H3/t5-,6-/m1/s1
InChI key
ROZOUYVVWUTPNG-PHDIDXHHSA-N
Application
(-)-Dimethyl 2,3-O-isopropylidene-L-tartrate may be used as a starting material in the total synthesis of (+)-migrastatin and also in the synthesis of a structural analog of S-ribosylhomocysteinase (LuxS), which acts as a potent competitive inhibitor against LuxS.
Valuable building block for TADDOL chiral auxiliaries, dipyridine ligands, and threitols.
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
Eyeshields, Gloves
Regulatory Information
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Design and synthesis of substrate and intermediate analogue inhibitors of S-ribosylhomocysteinase.
Shen G, et al.
Journal of Medicinal Chemistry, 49(10), 3003-3011 (2006)
Angewandte Chemie (International Edition in English), 30, 99-99 (1991)
Organic Syntheses, 68, 92-92 (1990)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 359068-5ML | 04061837640148 |
| 359068-25ML | 04061838348920 |