6612-63-1

Usage

Uses

Used in Pharmaceutical Industry:
.beta.-D-Glucopyranoside, phenylmethyl 1-thio-, tetraacetate is used as a protecting group for sugar molecules in the pharmaceutical industry for the production of various drugs. .beta.-D-Glucopyranoside, phenylmethyl 1-thio-, tetraacetate helps prevent unwanted reactions during the synthesis process, ensuring the stability and protection of the sugar molecules.
Used in Organic Synthesis:
In the field of organic synthesis, .beta.-D-Glucopyranoside, phenylmethyl 1-thio-, tetraacetate is used as a protecting group for sugar molecules. This allows chemists to carry out various reactions without affecting the sugar's functional group, which is crucial for the synthesis of complex organic compounds, including pharmaceuticals and other fine chemicals.

InChI:InChI=1/C21H26O9S/c1-12(22)26-10-17-18(27-13(2)23)19(28-14(3)24)20(29-15(4)25)21(30-17)31-11-16-8-6-5-7-9-16/h5-9,17-21H,10-11H2,1-4H3

Upstream product

• 19879-84-6 O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose 
• 100-44-7 benzyl chloride 
• 127066-70-0 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate 
• 6921-34-2 benzylmagnesium chloride 
• 15018-22-1 benzyl mercaptan zinc salt 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 100-53-8 phenylmethanethiol 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 14204-26-3 N-(benzylthio)phthalimide 
• 1394124-53-8 S-benzyl 4-fluorobenzenesulfonothioate 
• 16601-01-7 benzenethiosulfonic acid S-benzyl ester 
• 16601-02-8 S-benzyl 4-methylbenzenethiosulfonate 
• 7559-62-8 S-benzyl methanethiosulfonate 

Downstream Products

• 1179891-90-7 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 158419-97-7 benzyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 216871-85-1 (2R,3R,4S,5R)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-[1-phenyl-meth-(Z)-ylidene]-tetrahydro-pyran 
• 216871-90-8 (2R,3S,4S,5R)-2-Hydroxymethyl-6-[1-phenyl-meth-(Z)-ylidene]-tetrahydro-pyran-3,4,5-triol 
• 216871-80-6 benzyl S,S-dioxo-1-thio-2,3,4,6-tetra-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 
• 437758-21-9 benzyl S,S-dioxo-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions

A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.

Direct, stereoselective thioglycosylation enabled by an organophotoredox radical strategy

While strategies involving a 2e- transfer pathway have dictated glycosylation development, the direct glycosylation of readily accessible glycosyl donors as radical precursors is particularly appealing because of high radical anomeric selectivity and atom- and step-economy. However, the development of the radical process has been challenging owing to notorious competing reduction, elimination and/or SN side reactions of commonly used, labile glycosyl donors. Here we introduce an organophotocatalytic strategy through which glycosyl bromides can be efficiently converted into corresponding anomeric radicals by photoredox mediated HAT catalysis without a transition metal or a directing group and achieve highly anomeric selectivity. The power of this platform has been demonstrated by the mild reaction conditions enabling the synthesis of challenging α-1,2-cis-thioglycosides, the tolerance of various functional groups and the broad substrate scope for both common pentoses and hexoses. Furthermore, this general approach is compatible with both sp2 and sp3 sulfur electrophiles and late-stage glycodiversification for a total of 50 substrates probed.

Photochemical Functionalization of Heterocycles with EBX Reagents: C?H Alkynylation versus Deconstructive Ring Cleavage**

The development of novel methodologies for the functionalization of saturated heterocycles is highly desirable. Herein, we report a cheap and efficient photochemical method for the C?H functionalization of saturated O-heterocycles, as well as the deconstructive ring-cleavage of S-heterocycles, employing hypervalent iodine alkynylation reagents (ethynylbenziodoxolones, EBX). This photochemical alkynylation is performed utilizing phenylglyoxylic acid as the photoinitiator, leading to the corresponding products in good to high yields, under household fluorescent light bulb irradiation. When O-heterocycles were employed, the expected α-C?H alkynylation took place. In contrast, oxidative ring-opening to form a thioalkyne and an aldehyde was observed with S-heterocycles. Preliminary mechanistic experiments are presented to give first insights into this puzzling divergent reactivity.

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.

Remote Activation of Disarmed Thioglycosides in Latent-Active Glycosylation via Interrupted Pummerer Reaction

S-glycosides, S-2-(2-propylthio)benzyl (SPTB) glycosides, were converted to the corresponding oxidized glycosyl donors, S-2-(2-propylsulfinyl)benzyl (SPSB) glycosides, by simple and selective oxidation. Treatment of disarmed SPSB donor and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. Meanwhile, observation of thiosulfinate, thiosulfonate, and disulfide suggested that the leaving group was activated via an interrupted Pummerer reaction. The disarmed SPSB thioglycosyl donors could be selectively activated in the presence of various thioglycosides with remote activation mode. Finally, two natural hepatoprotective glycosides, Leonoside E and Leonuriside B, were efficiently synthesized in a convergent manner with this newly developed method.

Solid phase synthesis of glycopeptides using Shoda's activation of unprotected carbohydrates

An expedient and simple protocol to access S-linked glycopeptides by Fmoc SPPS using unprotected carbohydrates is reported. The utility of the method was demonstrated with the solid phase synthesis of a MUC1 fragment (20 mer) containing two glycosylation sites that were substituted with S-linked glycans. The Royal Society of Chemistry.

Towards dynamic drug design: Identification and optimization of β-galactosidase inhibitors from a dynamic hemithioacetal system

A discovery strategy relying on the identification of fragments through resolution of a constitutional dynamic system, coupled to subsequent static ligand design and optimization, is demonstrated. The strategic design and synthesis of the best molecular fragments identified from a dynamic hemithioacetal system into static ligand structures yielded a range of β-galactosidase inhibitors. Two series of structures mimicking the hemithioacetal motif were envisaged: thioglycosides and C-glycosides. Inhibition studies provided important structural information for the two groups, and 1-thiobenzyl-b-d-galactopyranoside demonstrated the best inhibitory effects.

Diastereoselective thioglycosylation of peracetylated glycosides catalyzed by in situ generated iron(III) iodide from elemental iodine and iron

A facile in situ preparation of Fe(III) iodide from cheap, abundant elemental iodine and iron metal served as an efficient catalyst for the thioglycosylation of peracetylated glycosides with various alkyl and aryl mercaptans. Due to neighboring participation, the anomerically pure β-thioglycosides were obtained in good to high yields with exclusive diastereocontrol.

Involvement of the S-aglycon in the conformational preferences of thioglucosides

The conformational preferences of two series of alkyl β-d-thioglucopyranosides in solution were investigated by NMR and CD. The rotamer populations of the hydroxymethyl group were found to depend on the structural nature of the S-aglycon. The population of the gt rotamer increased and that of the gg rotamer decreased as the alkyl group attached to the S atom increased in size. These rotamer populations have a linear correlation with the Taft' steric parameters, the nS s(-) σC s(-) O* exo-anomeric interaction may express these rotational preferences. Comparative analysis of the hydroxymethyl populations between alkyl O- and S-glucosides revealed identical or slightly higher gt and smaller gg populations for the latter compounds.