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
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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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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