TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE

TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE - Names and Identifiers

Name	[(2S,3S,4S,5R,6S)-6-bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)tetrahydropyran-2-yl]methyl 2,2-dimethylpropanoate
Synonyms	Canagliflozin Intermediate3 TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE 2,3,4,6-Tetra-O-pivaloyl-a-D-glucopyranosylbromide 2,3,4,6-Tetra-O-Pivaloyl-α-D-GlucopyranosylBromide 2,3,4,6-tetra-O-pivaloyl-alpha-D-glucopyranosylbromide 2,3,4,6-TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE 2,3,4,6-Tetra-O-Pivaloyl-Alpha-D-Glucopyranosyl Bromide TETRAKIS(2,2-DIMETHYLPROPANOATE)-A-D-GLUCOPYRANOSYL BROMIDE α-L-altropyranosyl bromide, tetrakis(2,2-dimethylpropanoate) 2,3,4,6-Tetra-O-pivaloyl-a-D-glucopyranosyl bromide (stabilised with CaCO3) (2R,3R,4S,5R,6R)-2-BroMo-6-((pivaloyloxy)Methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-diMethylpropanoate) [(2S,3S,4S,5R,6S)-6-broMo-3,4,5-tris(2,2-diMethylpropanoyloxy)tetrahydropyran-2-yl]Methyl2,2-diMethylpropanoate [(2S,3S,4S,5R,6S)-6-bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)tetrahydropyran-2-yl]methyl 2,2-dimethylpropanoate
CAS	81058-27-7
EINECS	686-241-8
InChI	InChI=1/C26H43BrO9/c1-23(2,3)19(28)32-13-14-15(34-20(29)24(4,5)6)16(35-21(30)25(7,8)9)17(18(27)33-14)36-22(31)26(10,11)12/h14-18H,13H2,1-12H3/t14-,15-,16-,17+,18+/m0/s1

TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE - Physico-chemical Properties

Molecular Formula	C26H43BrO9
Molar Mass	579.53
Density	1.22±0.1 g/cm3(Predicted)
Melting Point	147-148°C
Boling Point	530.5±50.0 °C(Predicted)
Flash Point	274.6°C
Solubility	Chloroform (Sparingly)
Vapor Presure	2.45E-11mmHg at 25°C
Appearance	Solid
Color	White to Off-White
Storage Condition	Inert atmosphere,2-8°C
Stability	Light Sensitive, Moisture Sensitive
Refractive Index	1.494

TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing.

TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE - Reference Information

introduction

2,3,4,6-O-tetra-pentanyl-alpha-D-bromo-glucopyranose can be used to prepare canagliflozin. Canaglifloin Canagliflozin is the first SGLT2 inhibitor drug approved by FDA. It can reduce blood sugar by decomposing glucose and excreting it through the kidneys. It has broad prospects for the treatment of adult type 2 diabetes.

preparation method

using ALPHA-D-glucose as raw material, after reacting with tervaloyl chloride to protect all hydroxyl groups, then reacting with zinc bromide and trimethylbromosilane at -10 ℃ to form intermediate 4, and adding a small amount of thionyl chloride to the process of protecting group, so that the dosage of tervaloyl chloride is reduced by half, and the yield is not affected, the two-step yield is above 82%, and the total yield is more than 67%.

Last Update：2024-04-09 21:04:16