32384-65-9, tetrakis-O-(trimethylsilyl)-D-glocono 1,5-Lactone ,CAS:32384-65-9

32384-65-9,tetrakis-O-(trimethylsilyl)-D-glocono 1,5-Lactone ,
CAS:32384-65-9
C18H42O6Si4 / 466.86
MFCD22665922

2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-1,5-lactone

四-O-三甲基硅基-D-葡萄糖酸内酯

2,3,4,6-Tetra-O-trimethylsilyl-D-glucono-1,5-lactone is a synthetic building block which has been used to prepare C-glucosides via the nucleophilic addition of a suitably functionalised aryllithium reagent, followed by a triethylsilane reduction. Notable examples of this include the synthesis of C-glycoside intermediates which have been further elaborated to afford canagliflozin, bexagliflozin and dapagliflozin which inhibit sodium-dependant glucose co-transporter 2 (SGLT2) and are of interest as antidiabetic agents.

CAS Number	32384-65-9
Product Name	(3R,4S,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
IUPAC Name	(3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-2-one
Molecular Formula	C18H42O6Si4
Molecular Weight	466.86 g/mol
InChI	InChI=1S/C18H42O6Si4/c1-25(2,3)20-13-14-15(22-26(4,5)6)16(23-27(7,8)9)17(18(19)21-14)24-28(10,11)12/h14-17H,13H2,1-12H3/t14-,15-,16+,17-/m1/s1
InChI Key	VNGTZLYNGGLPIZ-WCXIOVBPSA-N
SMILES	C[Si](C)(C)OCC1C(C(C(C(=O)O1)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C
Synonyms	(3R,4S,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2h-pyran-2-o
Canonical SMILES	C[Si](C)(C)OCC1C(C(C(C(=O)O1)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C
Isomeric SMILES	C[Si](C)(C)OC[C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C