58479-62-2

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol is used as a potential pharmaceutical agent for its unique structure and biological activity. (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol's specific stereochemistry and functional groups may allow it to interact with biological targets in ways that could lead to the development of new drugs or therapeutic agents.
Used in Chemical Industry:
In the chemical industry, (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol can be utilized as a building block or intermediate in the synthesis of more complex molecules. Its unique structure and functional groups may enable the creation of novel chemical compounds with specific properties for various applications, such as materials science, catalysis, or specialty chemicals.

Upstream product

• 58479-67-7 methyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 
• 154859-16-2 <2'R,2''R,6'R,6''R> methyl 6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-di-(2-oxoethyl)octahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 97-30-3 methyl-alpha-D-glucopyranoside 

Downstream Products

• 131511-71-2 (3aR,4S,6R,7R,7aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxy-2,2,2-triphenyl-tetrahydro-1,3,5-trioxa-2λ⁵-phospha-inden-7-ol 
• 131511-72-3 (3aR,4R,6S,7R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-2,2,2-triphenyl-tetrahydro-1,3,5-trioxa-2λ⁵-phospha-inden-7-ol 
• 154859-15-1 <2'R,2''R,6'R,6''R> methyl 6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-diallyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 154859-14-0 <2'R,2''R,6'R,6''R> methyl 4-O-acetyl-6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 154859-10-6 <2'R,2''R,6'R,6''R> methyl 6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 154859-11-7 <2'S,2''S,6'S,6''S> methyl 6-O-(tert-butyldiphenylsilyl)-3-O,4-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 130359-45-4 methyl 2-O-acetyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 
• 130359-43-2 methyl 4-O-acetyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 
• 130359-44-3 methyl 3-O-acetyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 
• 58479-67-7 methyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 
• 148657-21-0 methyl 2-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-glucopyranoside 
• 164398-16-7 <2'S,2''S,4'S,4''S> methyl 6-O-(tert-butyldiphenylsilyl)-3-O,4-O-(4',4''-dimethyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 189825-41-0 methyl 6-O-(tert-butyldiphenylsilyl)-2,3,4-tri-O-(methoxymethyl)-α-D-glucopyranoside 
• 261967-62-8 Isophthalic acid 1-[(2S,3R,4S,5S,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-4,5-dihydroxy-2-methoxy-tetrahydro-pyran-3-yl] ester 3-((2R,3S,4S,5R,6S)-3,4,5-trimethoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester 

Relevant academic research and scientific papers

Synthesis of amphiphilic A3B mikto-arm copolymers from a sugar core: Combination of hydrophobic PCL and hydrophilic glycopolymers for biocompatible nanovector preparation

Amphiphilic A3B mikto-arm copolymers have been synthesized using a t-butyl-diphenyl silyl-based methylglucoside derivative. The latter has been first used as initiator for the polymerization of ε-caprolacto ne leading to three-arm starshaped st

Orthogonal protection of saccharide polyols through solvent-free one-pot sequences based on regioselective silylations

tert-Butyldimethylsilyl (TBDMS) and tert-butyldiphenylsilyl (TBDPS) are alcohol protecting groups widely employed in organic synthesis in view of their compatibility with a wide range of conditions. Their regioselective installation on polyols generally r

Application of ball milling technology to carbohydrate reactions: I. Regioselective primary hydroxyl protection of hexosides and nucleoside by planetary ball milling

Dry ball milling of hexosides with trityl chloride in the presence of DABCO or Na2CO3 has been found to result in their complete conversion to the respective 6-O-trityl ethers. Further wet grinding of the reaction mixture with Ac2O in the presence of DMAP led to the respective fully protected hexosides in good to excellent yields after isolation. It has been found to be an effective one-pot two-step synthesis under solvent-free condition. The speed of homogenization has been shown to highly influence the rate and outcome of the reaction, and commercially available planetary ball mill has been proved to be very convenient for carrying out the reaction under standardized and reproducible conditions.

Directing-protecting groups for carbohydrates. Design, conformational study, synthesis and application to regioselective functionalization

A novel concept of regioselective transformation of secondary hydroxyl groups in carbohydrates is presented. First, the relative reactivity of the free hydroxyl groups of onoprotected d-glucose derivatives was assessed using acetylation as a model reactio

Imidazole-promoted 1,4-migration of the tert-butyldiphenylsilyl group: Influence on the selectivity control of the silylation reactions of carbohydrate OH groups

The regioselective protection of secondary hydroxy groups of gluco-, galacto-, manno-, rhamno- and fucopyranosides using TBDPSCl with imidazole in DMF has been studied. It was found that the relative spatial arrangement of the OH groups modulates the silylation selectivity which arises from the combination of kinetic factors and the intramolecular migrations of the secondary TBDPS groups. The rearrangement of the TBDPS groups has a much larger effect on the α-D-manno- and α-L-rhamnopyranosides, allowing the protection of the OH groups at positions 2, 3 or 2 and 4, in synthetically useful yields, by changing the reaction conditions. The relative reactivity of the secondary OH groups seems particularly likely to be governed by steric factors. This trend provides a valuable approach to the synthesis of 3-O-tert-butyldiphenylsilyl-1-thio-β-L-fucopyranoside.

Solution- and solid-phase oligosaccharide synthesis using glucosyl iodides: a comparative study

Glycosyl iodide donors have been used in both solid- and solution-phase syntheses yielding α-(1->6)-linked glucosyl oligomers in highly efficient protocols. While the solid-phase strategy offers advantages in terms of ease of purification, it requires a t

Synthesis of aminophosphonate haptens for an aminoacylation reaction between methyl glucoside and a β-alanyl ester

Two 2-aminophosphonate haptens derived from methyl α-D-glucopyranoside were synthesized to mimic the transition-state of a transesterification reaction between methyl α-D-glucopyranoside and 4-nitrophenylester of tert-BOC-β-alanine. Two sets of monoclonal

Stereochemical study of the CD spectral differences between anomers of alkyl glucopyranosides

Slightly different chair conformation geometries were demonstrated to be the origin of the C-D spectral differences observed in anomers of alkyl glucopyranosides. The study, using methyl glucopyranoside derivatives as model compounds, showed excellent agreement between CD data, 1H NMR data, and semiempirical calculations, and the geometries found explained satisfactorily the higher amplitudes observed for the β-anomers of tetrachromophorically substituted alkyl glucopyranosides. The pairwise interactions involving the chromophore at C2, the 2/3, 2/4 and 2/6, were the most dependent on the anomeric configuration, the 2/4 interaction even showing opposite CD signs for the anomers. In addition, the 2/3 pairwise interaction was revealed to be independent of the structural nature of the aglycon.

Dispiroketals in Synthesis (Part 17): Regioselective Protection of D-Glucopyranoside, D-Galactopyranoside and D-mannopyranoside Substrates

Chiral recognition of enantiomeric trans-1,2-diol relationships leading to regioselective formation of 1,8,13,16-tetraoxadispirohexadecanes (dispiroketals) of various D-glucopyranoside, D-galactopyranoside and D-mannopyranoside substrates is desc

Some Mechanistic Aspects of Carbohydrate Electrochemistry

The electroreductive conversion of carbohydrates leads to anions the reactions of which with alkylating or acylating reagents results in the formation of ether or ester derivatives.The obtained substitution patterns are influenced by the acidity of the di