377090
(−)-2,3-O-Isopropylidene-D-erythronolactone
98%
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About This Item
Empirical Formula (Hill Notation):
C7H10O4
CAS Number:
Molecular Weight:
158.15
Beilstein:
1282952
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
optical activity
[α]20/D −118°, c = 1 in H2O
mp
67-69 °C (lit.)
SMILES string
CC1(C)O[C@@H]2COC(=O)[C@@H]2O1
InChI
1S/C7H10O4/c1-7(2)10-4-3-9-6(8)5(4)11-7/h4-5H,3H2,1-2H3/t4-,5-/m1/s1
InChI key
WHPSMBYLYRPVGU-RFZPGFLSSA-N
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Application
Undergoes Aldol condensations with silyl ketene acetals. Employed in spiroannulated carbohydrate synthesis. Convergent syntheses of a hydroxylated indolizidine, carbohydrate substituted benzoquinones, and of the oxazole segment of calyculin have been accomplished using this chiral synthon.
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
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Find documentation for the products that you have recently purchased in the Document Library.
Perri, S.T. et al.
The Journal of Organic Chemistry, 54, 2032-2032 (1989)
Tetrahedron, 50, 3333-3333 (1994)
Tetrahedron, 50, 1111-1111 (1994)
M.-P. Heitz et al.
The Journal of Organic Chemistry, 54, 2591-2591 (1989)
A.B. Smith et al.
Tetrahedron Letters, 32, 4859-4859 (1991)
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