Roche ester

Roche ester
	; (R)- and (S)-enantiomers of Roche ester
Names
	Preferred IUPAC name Methyl 3-hydroxy-2-methylpropanoate
Identifiers
CAS Number	72657-23-9 (R); 80657-57-4 (S);
3D model (JSmol)	(R): Interactive image; (S): Interactive image;
ChemSpider	4482250 (R); 8368063 (S);
ECHA InfoCard	100.250.015
PubChem CID	5324733 (R); 10192563 (S);
UNII	569FQ3X7KG ;
CompTox Dashboard (EPA)	DTXSID90993497 ;
	InChI (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;
	SMILES (R): C[C@H](CO)C(=O)OC; (S): C[C@@H](CO)C(=O)OC;
Properties
Chemical formula	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). Infobox references

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

^ 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.
^ 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.
^ 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.