7473-36-1

Basic information

• Product Name: ETHYL BETA-D-THIOGLUCOSIDE
• Synonyms: ETHYL BETA-D-THIOGLUCOSIDE;ethyl B-D-thioglucoside;Ethyl 1-thio-b-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-ETHYLSULFANYL-6-HYDROXYMETHYL-TETRAHYDRO-PYRAN-3,4,5-TRIOL;ethyl β-d-thioglucoside;ETHYL 1-THIO-β-D-GLUCOPYRANOSIDE;ethyl-beta-D-1-thioglucopyranoside;Ethyl-β-D-thio-glucopyranosid
• CAS NO: 7473-36-1
• Molecular Formula: C₈H₁₆O₅S
• Molecular Weight: 224.27
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates;Carbohydrates A to;Carbohydrates D-FBiochemicals and Reagents;Monosaccharide;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
• Mol File: 7473-36-1.mol
• Article Data: 50

Chemical Properties

• Melting Point: 87-89°C
• Boiling Point: 440.8 °C at 760 mmHg
• Flash Point: 220.4 °C
• Appearance: /
• Density: 1.43 g/cm³
• Vapor Pressure: 1.28E-09mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: −20°C
• Solubility: Dichloromethane, Methanol
• PKA: 13.00±0.70(Predicted)
• CAS DataBase Reference: ETHYL BETA-D-THIOGLUCOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL BETA-D-THIOGLUCOSIDE(7473-36-1)
• EPA Substance Registry System: ETHYL BETA-D-THIOGLUCOSIDE(7473-36-1)

Safety Data

• Hazardous Substances Data: 7473-36-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C8H16O5S/c1-2-14-8-7(12)6(11)5(10)4(3-9)13-8/h4-12H,2-3H2,1H3

Upstream product

• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 75-08-1 ethanethiol 
• 604-69-3 β-D-glucose pentaacetate 
• 492-61-5 β-D-glucose 
• 83-87-4 D-glucose pentaacetate 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 2280-44-6 D-Glucose 
• 50-99-7 D-glucose 
• 4137-33-1 ethyl 1-thio-α-D-glucofuranoside 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 1290085-45-8 2,3:4,5-di-O-isopropylidene-β-D-glucoseptanose 
• 1379587-23-1 ethyl 1-thio-2,3:4,5-di-O-isopropylidene-α-D-glucoseptanoside 
• 1379587-24-2 O-(2,3:4,5-di-O-isopropylidene-β-D-glucoseptanosyl) trichloroacetimidate 

Downstream Products

• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 219536-50-2 ethyl 4,6-O-benzylidene-1-thio-α-D-glucopyranoside 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 136597-23-4 ethyl 3-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 39483-51-7 ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 152964-72-2 ethyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 454664-78-9 ethyl 2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 173935-67-6 ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 218937-71-4 ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 152964-79-9 ethyl 2,3,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 38992-99-3 methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 151123-93-2 Ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-glucopyranoside 
• 151072-56-9 2-O-Benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranosyl chloride 

Relevant articles and documents

A versatile approach to the synthesis of glycans containing mannuronic acid residues

Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linkedviaβ-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3-O-benzoyl group is also reported.

GLUCOSE TRIPTOLIDE CONJUGATES AND USES THEREOF

A major hurdle in the treatment of cancer is chemoresistance induced under hypoxia that is characteristic of tumor microenvironment. Triptolide, a potent inhibitor of eukaryotic transcription, possesses potent antitumor activity. However, its clinical potential has been limited by toxicity and water solubility. To address those limitations of triptolide, the present disclosure designed and synthesized glucose-triptolide conjugates (glutriptolides) and demonstrated their antitumor activity in vitro and in vivo. The glutriptolides disclosed herein possess improved stability in human serum, greater selectivity towards cancer over normal cells and increased potency against cancer cells. Importantly, the glutriptolides are more potent against cancer cells under hypoxic conditions in contrast to existing cytotoxic drugs. These glutriptolides also exhibit sustained antitumor activity, prolonging survival in a prostate cancer metastasis animal model. Together, these findings suggest a new strategy to overcome chemoresistance through conjugation of cytotoxic agents to glucose.

One-Pot Relay Glycosylation

A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the in situ generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one pot. A wide range of substrates are well-accommodated to furnish both linear and branched oligosaccharides. The synthetic utility and advantage of this method have been demonstrated by rapid access to naturally occurring phenylethanoid glycoside kankanoside F and resin glycoside merremoside D.