Jump to content

Roche ester

From Wikipedia, the free encyclopedia
Roche ester

(R)- and (S)-enantiomers of Roche ester
Names
Preferred IUPAC name
Methyl 3-hydroxy-2-methylpropanoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.250.015 Edit this at Wikidata
UNII
  • (R): InChI=1S/C5H10O3/c1-4(3-6)5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1
    Key: ATCCIZURPPEVIZ-SCSAIBSYSA-N
  • (S): InChI=1S/C5H10O3/c1-4(3-6)5(7)8-2/h4,6H,3H2,1-2H3/t4-/m0/s1
    Key: ATCCIZURPPEVIZ-BYPYZUCNSA-N
  • (R): C[C@H](CO)C(=O)OC
  • (S): C[C@@H](CO)C(=O)OC
Properties
C5H10O3
Molar mass 118.13 gmol−1
Density 1.071 g/mL
Boiling point 74 °C (165 °F; 347 K) at 10 mmHg
Hazards
Flash point 80 °C (176 °F; 353 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Roche ester (methyl 3-hydroxy-2-methylpropionate) is a chemical compound with formula C5H10O3. It can exist as two enantiomers. Both are commercially available and have been widely used as starting blocks for the synthesis of many targets including dictyostatin,[1] discodermolide[2] and spongidepsin.[3]

References

[edit]
  1. ^ Shin, Youseung; Fournier, Jean-Hugues; Fukui, Yoshikazu; Brückner, Arndt; Curran, Dennis (2004). "Total Synthesis of (−)-Dictyostatin: Confirmation of Relative and Absolute Configurations". Angewandte Chemie International Edition. 43 (35). Wiley: 4634–4637. doi:10.1002/anie.200460593. PMID 15316999.
  2. ^ Paterson, Ian; Florence, Gordon (2003). "The Development of a Practical Total Synthesis of Discodermolide, a Promising Microtubule-Stabilizing Anticancer Agent". European Journal of Organic Chemistry. 2003 (12). Wiley: 2193–2208. doi:10.1002/ejoc.200300061.
  3. ^ Ferrié, Laurent; Reymond, Sébastien; Capdevielle, Patrice; Cossy, Janine (2006). "Total Synthesis of (−)-Spongidepsin". Organic Letters. 8 (16). American Chemical Society: 3441–3443. doi:10.1021/ol061029w. PMID 16869630.
[edit]