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377090

Sigma-Aldrich

(−)-2,3-O-Isopropylidene-D-erythronolactone

98%

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About This Item

Empirical Formula (Hill Notation):
C7H10O4
CAS Number:
25581-41-3
Molecular Weight:
158.15
Beilstein:
1282952
MDL number:
MFCD00134440
UNSPSC Code:
12352201
PubChem Substance ID:
24863491
NACRES:
NA.22

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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Certificates of Analysis (COA)

Lot/Batch Number
BGBC3327V
BGBC2588V
BGBB8792
MKBG7969V
MKBF8423V

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Tetrahedron, 50, 1111-1111 (1994)
Perri, S.T. et al.
The Journal of Organic Chemistry, 54, 2032-2032 (1989)
Tetrahedron, 50, 3333-3333 (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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