87470-70-0

Basic information

• Product Name: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-
• Synonyms: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-;Beta-D-Glucopyranoside,phenyl2,3-bis-O-(phenylMethyl)-4,6-O-[(R)-phenylMethylene]-1-thio-
• CAS NO: 87470-70-0
• Molecular Formula: C₃₃H₃₂O₅S
• Molecular Weight: 540.677
• Mol File: 87470-70-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 143-144 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• Boiling Point: 675.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-(CAS DataBase Reference)
• NIST Chemistry Reference: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-(87470-70-0)
• EPA Substance Registry System: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-(87470-70-0)

Safety Data

• Hazardous Substances Data: 87470-70-0(Hazardous Substances Data)

Usage

Description

B-D-Glucopyranoside, phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiois a protected glucopyranoside that serves as a building block for the synthesis of complex carbohydrates. B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiofeatures β-phenylthio, 2 and 3 benzyl, and 4,6-benzylidine protecting groups, which play a crucial role in the synthesis process.

Uses

Used in Pharmaceutical Industry:
B-D-Glucopyranoside, phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiois used as a building block for the synthesis of complex carbohydrates in the pharmaceutical industry. The presence of β-phenylthio, 2 and 3 benzyl, and 4,6-benzylidine protecting groups allows for the creation of intricate carbohydrate structures that can be utilized in the development of new drugs and therapies.
Used in Chemical Research:
In the field of chemical research, B-D-Glucopyranoside, phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiois used as a valuable building block for the synthesis of complex carbohydrates. Researchers can leverage the compound's protecting groups to explore new methods and techniques in carbohydrate chemistry, potentially leading to breakthroughs in various applications.
Used in Material Science:
B-D-Glucopyranoside, phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiois also used in material science for the development of advanced materials with unique properties. B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-'s protecting groups enable the synthesis of complex carbohydrate structures that can be incorporated into materials with specific characteristics, such as improved biocompatibility or enhanced functionality.
Overall, B-D-Glucopyranoside, phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiois a versatile compound with a wide range of applications across various industries, including pharmaceuticals, chemical research, and material science. Its unique structure and protecting groups make it an invaluable building block for the synthesis of complex carbohydrates and the development of innovative products and solutions.

Upstream product

• 100-39-0 benzyl bromide 
• 108-98-5 thiophenol 
• 13992-16-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 13992-15-9 phenyl-1-thio-α-D-glucopyranoside 
• 604-68-2 α-D-glucopyranose peracetylate 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 2936-70-1 phenyl 1-thio-D-glucopyranoside 
• 71676-30-7 (4aR,6R,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 71676-30-7 (2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 100-44-7 benzyl chloride 
• 83-87-4 D-glucose pentaacetate 
• 100-52-7 benzaldehyde 

Downstream Products

• 1072523-01-3 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene 
• 1403351-19-8 2,3-di-O-benzyl-4,6-O-benzylidene-1-(2-oxo-2-phenylethyl)-α-Dglucopyranose 
• 1403351-20-1 [(1R)-2-oxo-1,3-diphenyl-1-(phenylthiomethyl)ethyl] 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 1352827-06-5 methyl (4-O-benzoyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

The assembly of complex bacterial glycans presenting rare structural motifs and cis-glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions i

Conformationally Switchable Glycosyl Donors

Glycosyl donors functionalized with 2,2′-bipyridine moieties on the 3-OH and 6-OH or the 2-OH and 4-OH undergo a conformational change when forming 1:1 complexes with Zn2+ ions. The pyranoside ring of the zinc complexes adopted axial-rich skew boat conformations. The reactivities of the two glycosyl donors were investigated by performing a series of glycosylations in the presence or absence of Zn2+ ions. These glycosylations suggested a decrease in reactivity when binding Zn2+. The conformational effect of binding Zn2+ was therefore studied using a third glycosyl donor, unable to undergo conformational changes when binding Zn2+. From competition experiments, it was observed that the binding-induced conformational change increased the reactivity slightly compared to the glycosyl donor unable to undergo a conformational change.

Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates

In the presence of a diarylborinic acid catalyst, glycosyl methanesulfonates engage in regio- and stereoselective couplings with partially protected pyranoside and furanoside acceptors. The methanesulfonate donors are prepared in situ from glycosyl hemiacetals, and are coupled under mild, operationally simple conditions (amine base, organoboron catalyst, room temperature). The borinic acid catalyst not only influences site-selectivity via activation of 1,2- or 1,3-diol motifs, but also has a pronounced effect on the stereochemical outcome: 1,2-trans-linked disaccharides are obtained selectively in the absence of neighboring group participation. Reaction progress kinetic analysis was used to obtain insight into the mechanism of glycosylation, both in the presence of catalyst and in its absence, while rates of interconversion of methanesulfonate anomers were determined by NMR exchange spectroscopy (EXSY). Together, the results suggest that although the uncatalyzed and catalyzed reactions give rise to opposite stereochemical outcomes, both proceed by associative mechanisms.