224778-57-8

Basic information

• Product Name: 1,2,3,4-tetra-O-acetyl-6-O-tert-butyldiphenylsilyl-α/β-D-glucopyranose
• Synonyms: 1,2,3,4-tetra-O-acetyl-6-O-tert-butyldiphenylsilyl-α/β-D-glucopyranose
• CAS NO: 224778-57-8
• Molecular Weight: 586.711
• Mol File: 224778-57-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,2,3,4-tetra-O-acetyl-6-O-tert-butyldiphenylsilyl-α/β-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tetra-O-acetyl-6-O-tert-butyldiphenylsilyl-α/β-D-glucopyranose(224778-57-8)
• EPA Substance Registry System: 1,2,3,4-tetra-O-acetyl-6-O-tert-butyldiphenylsilyl-α/β-D-glucopyranose(224778-57-8)

Safety Data

• Hazardous Substances Data: 224778-57-8(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 108-24-7 acetic anhydride 
• 2280-44-6 D-Glucose 
• 108535-19-9 6-O-(tert-butyldiphenylsilyl)-D-glucopyranose 
• 65620-65-7 1,2,3,4-tetra-O-acetyl-D-glucopyranose 

Downstream Products

• 180072-36-0 2,3,4-tri-O-acetyl-6-O-[(1,1-dimethylethyl)diphenylsilyl]-α-D-glucopyranosyl bromide 
• 151797-32-9 3,4-di-O-acetyl-6-O-(tert-butyl diphenylsilyl)-D-glucal 

Relevant articles and documents

From Glucose to Polymers: A Continuous Chemoenzymatic Process

Efforts to synthesize degradable polymers from renewable resources are deterred by technical and economic challenges; especially, the conversion of natural building blocks into polymerizable monomers is inefficient, requiring multistep synthesis and chromatographic purification. Herein we report a chemoenzymatic process to address these challenges. An enzymatic reaction system was designed that allows for regioselective functional group transformation, efficiently converting glucose into a polymerizable monomer in quantitative yield, thus removing the need for chromatographic purification. With this key success, we further designed a continuous, three-step process, which enabled the synthesis of a sugar polymer, sugar poly(orthoester), directly from glucose in high yield (73 % from glucose). This work may provide a proof-of-concept in developing technically and economically viable approaches to address the many issues associated with current petroleum-based polymers.

Mitigation of Hydrophobicity-Induced Immunotoxicity by Sugar Poly(orthoesters)

Polymeric nanoparticles (NPs) derived from self-assemblies of amphiphilic polymers have demonstrated great potential in clinical applications. However, there are challenges ahead. Notably, immunotoxicity remains a major roadblock that deters the NPs from

Rapid preparation of variously protected glycals using titanium(III)

Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)2. This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. β-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.