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L15988 2,3-O-Isopropylidene-alpha,beta-D-ribofuranose

CAS Number
13199-25-2
Synonyms

Stock No. Size Price ($) Quantity Availability
L15988-03 1g 71.60
L15988-06 5g 284.00
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2,3-O-Isopropylidene-alpha,beta-D-ribofuranose

MDL
MFCD01075718

Chemical Properties

Formula
C8H14O5
Formula Weight
190.20
Storage & Sensitivity
Keep Cold.
Solubility
Soluble in acetone.

Applications

2,3-O-Isopropylidene-alpha,beta-D-ribofuranose is used as a pharmaceutical intermediate.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents.

Literature References

J.Grant Buchanan, Allan D. Dunn, Alan R. Edgar. Reaction of ethynylmagnesium bromide with 2,3-O-isopropylidene-D-ribose and 2,3:5,6-di-O-isopropylidene-D-mannofuranose: syntheses of glycofuranosylethynes. Carbohydrate Research. 1974, 36 (1), C5-C7.

N.A. Hughes.; P.R.H. Speakman. New isopropylidene derivatives of d-ribose: 1,2:3,4-di-O-isopropylidene-d-ribopyranose and 1,2-O-isopropylidene-d-ribopyranose. Carbohydrate Research. 1965, 1 (2), 171-175.

Reaction of this hemiacetal with various organometallic species provides routes to a number of synthetic targets, e.g.: (-)-5-epishikimic acid: Tetrahedron Lett., 35, 5505 (1994); J. Chem. Soc., Perkin 1, 1805 (1997), aminocyclopentitols: Tetrahedron: Asymmetry, 6, 1547 (1995), cyclopentane-type glycosidase inhibitors: J. Org. Chem., 61, 1354 (1996). Reaction with cysteamine leads to diastereomerically pure analogues of the alkaloids castanospermine and australine: Tetrahedron Lett., 37, 49 (1996).

Other References

Harmonized Tariff Code
2932.99
TSCA
No

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