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2,3,4,6-TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE

[(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

Molecular Formula: C26H43BrO9

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2,3,4,6-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

2,3,4,6-TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE - Physico-chemical Properties

Molecular FormulaC26H43BrO9
Molar Mass579.53
Density1.22±0.1 g/cm3(Predicted)
Melting Point147-148°C
Boling Point530.5±50.0 °C(Predicted)
Flash Point274.6°C
Solubility Chloroform (Sparingly)
Vapor Presure2.45E-11mmHg at 25°C
AppearanceSolid
ColorWhite to Off-White
Storage ConditionInert atmosphere,2-8°C
StabilityLight Sensitive, Moisture Sensitive
Refractive Index1.494

2,3,4,6-TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE - Risk and Safety

Hazard SymbolsXi - Irritant
Irritant
Risk Codes36/37/38 - Irritating to eyes, respiratory system and skin.
Safety DescriptionS26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36 - Wear suitable protective clothing.

2,3,4,6-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
2,3,4,6-TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE
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SHANGHAI ACMEC BIOCHEMICAL TECHNOLOGY CO., LTD.
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CAS: 81058-27-7
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Product Name: Tetra-O-pivaloyl-Alpha-D-glucopyranosyl bromide Visit Supplier Webpage Request for quotation
CAS: 81058-27-7
Tel: 18301782025
Email: 3008007409@qq.com
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SHANGHAI ACMEC BIOCHEMICAL TECHNOLOGY CO., LTD.
Spot supply
Product Name: Tetra-O-pivaloyl-Alpha-D-glucopyranosyl bromide Visit Supplier Webpage Request for quotation
CAS: 81058-27-7
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922 Click to send a QQ message
Wechat: 18621343501
WhatsApp: +86-18621343501
Shanghai Macklin Biochemical Co., Ltd
Spot supply
Product Name: Tetra-O-pivaloyl-α-D-glucopyranosyl Bromide Visit Supplier Webpage Request for quotation
CAS: 81058-27-7
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328 Click to send a QQ message
WhatsApp: +86-18821248368
Shanghai Yuanye Bio-Technology Co., Ltd.
Product Name: Tetra-O-pivaloyl-Alpha-D-glucopyranosyl bromide Visit Supplier Webpage Request for quotation
CAS: 81058-27-7
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409 Click to send a QQ message
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2,3,4,6-TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE
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