5-溴-4-氯-3-吲哚-β-D-吡喃葡萄糖糖苷

5-溴-4-氯-3-吲哚-β-D-吡喃葡萄糖糖苷 - Names and Identifiers

Name	5-Bromo-4-chloro-3-indolyl-beta-D-glucopyranoside
Synonyms	X-Glc, X-glucoside 5-Bromo-4-chloro-3-indoxylglucoside 5-Bromo-4-Chloro-3-Indolyl-Beta-D-Glucoside 5-Bromo-4-chloro-3-indolyl-beta-D-glucoside 5-Bromo-4-chloro-3-indolyl β-D-glucopyranoside 5-Bromo-4-chloroindol-3-yl-beta-D-glucopyranoside 5-Bromo-4-chloro-3-indolyl-beta-D-glucopyranoside 5-Bromo-4-chloro-1H-indol-3-yl β-D-glucopyranoside 4-Chloro-5-bromo-1H-indole-3-yl β-D-glucopyranoside 5-bromo-4-chloro-1H-indol-3-yl beta-D-glucopyranoside 5-BROMO-4-CHLORO-3-INDOLYL-β-D-GLUCOPYRANOSIDE (X-GLC) beta-D-Glucopyranoside, 5-bromo-4-chloro-1H-indol-3-yl 5-bromo-4-chloro-1H-indol-3-yl beta-L-galactopyranoside 5-BROMO-4-CHLORO-3-INDOLYL-BETA-D-GLUCOPYRANOSIDE (X-GLU) 5-BROMO-4-CHLORO-3-INDOLYL-b-D-GLUCO-PYRANOSIDE (X-GLU) extrapure (2S,3R,4S,5S,6R)-2-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
CAS	15548-60-4
EINECS	239-603-0
InChI	InChI=1/C14H15BrClNO6/c15-5-1-2-6-9(10(5)16)7(3-17-6)22-14-13(21)12(20)11(19)8(4-18)23-14/h1-3,8,11-14,17-21H,4H2/t8-,11+,12+,13-,14-/m0/s1
InChIKey	OPIFSICVWOWJMJ-OTXFOCTGSA-N

5-溴-4-氯-3-吲哚-β-D-吡喃葡萄糖糖苷 - Physico-chemical Properties

Molecular Formula	C14H15BrClNO6
Molar Mass	408.63
Density	1.882±0.06 g/cm3(Predicted)
Melting Point	249-251 °C
Boling Point	673.9±55.0 °C(Predicted)
Specific Rotation(α)	-81 º (c=1, DMF)
Flash Point	361.3°C
Solubility	DMF: 50mg/mL, clear, colorless to very faintly yellow
Vapor Presure	4.44E-19mmHg at 25°C
BRN	1552603
pKa	12.74±0.70(Predicted)
Storage Condition	−20°C
Refractive Index	1.731

5-溴-4-氯-3-吲哚-β-D-吡喃葡萄糖糖苷 - Risk and Safety

Safety Description	24/25 - Avoid contact with skin and eyes.
WGK Germany	3
FLUKA BRAND F CODES	8-10-21
HS Code	29389090

5-溴-4-氯-3-吲哚-β-D-吡喃葡萄糖糖苷 - Reference Information

trait	white microcrystalline powder.
use	5-bromo -4-chloro -3-indolyl-beta-D-glucopyranoside is a glycoside derivative, which has received extensive attention in the fields of medicine and chemical industry, and is also an enzyme substrate.
there are many synthetic methods for preparing	glycosides. the most commonly used synthetic methods are brominated glucose method and trichloroacetonitrile method. However, there are not many reports on the synthesis of 5-bromo-4-chloro-3-indolyl-beta-D-glucopyranoside. In this paper, 5-bromo-4-chloro-3-indolyl-beta-D-glucopyranoside was synthesized by using glucose as raw material and brominated glucose method and trichloroacetonitrile method. The synthesis reaction formula is as follows:
synthesis method	method 1: take 5-bromo -4-chlorine -3-indole -2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside and dissolve it in 15mL of methanol, cool to 0 ℃ in ice bath; Then add 3mL(0.5mol/L) of sodium methoxide methanol solution dropwise and stir for 5 hours at this temperature. After the reaction is over, pour the reaction solution into the pre-treated cation exchange resin (pretreatment method of cationic resin: rinse the resin with clear water first; Then soak in 5% hydrochloric acid for about 4 hours and wash to neutral. Soak in 5% sodium hydroxide solution for about 4 hours, wash with water to neutral; Finally, soak in 5% hydrochloric acid for 4 hours and wash to neutral), stir slowly for 5~10min, filter, rinse with methanol, evaporate the filtrate to remove the solvent to obtain 0.49g of white solid 5-bromo -4-chloro -3-indolyl-beta-D-glucopyranoside with a yield of 81.6% and a melting point of 86.5 ℃. Method 2: 40mg of compound 5 was dissolved in 5mL of methanol, cooled to 0 ℃ in an ice bath, then 5mL(0.2mol/L) of sodium methoxide methanol solution was added dropwise, and stirred at this temperature for 3 hours. After the reaction is over, pour the reaction solution into the pre-treated cation exchange resin (pretreatment method is the same as section 1.2.1) and stir slowly for 5-10min. Filter, rinse with methanol, the filtrate was distilled to remove the solvent to obtain 10mg of white solid, namely 5-bromo-4-chloro-3-indolyl-beta-D-glucopyranoside, with a yield of 40.3% and a melting point of 82.1 ℃.

Last Update：2024-04-09 21:11:58

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