53905-78-5

Basic information

• Product Name: 1,4-anhydro-D-glucitol tetraacetate
• Synonyms: 1,4-Anhydro-D-glucitol tetraacetate; 1,2,4,5-tetra-O-acetyl-3,6-anhydrohexitol
• CAS NO: 53905-78-5
• Molecular Formula: C₁₄H₂₀O₉
• Molecular Weight: 332.3032
• EINECS: 258-855-2
• Mol File: 53905-78-5.mol

Chemical Properties

• Boiling Point: 410.7°C at 760 mmHg
• Flash Point: 179.6°C
• Density: 1.26g/cm³
• Vapor Pressure: 5.92E-07mmHg at 25°C
• Refractive Index: 1.475
• CAS DataBase Reference: 1,4-anhydro-D-glucitol tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-anhydro-D-glucitol tetraacetate(53905-78-5)
• EPA Substance Registry System: 1,4-anhydro-D-glucitol tetraacetate(53905-78-5)

Safety Data

• Hazardous Substances Data: 53905-78-5(Hazardous Substances Data)

Usage

Derivation

Derived from D-glucitol (sorbitol)

Functionality

Used as a protecting group for hydroxyl groups in organic synthesis

Structure

Four acetyl groups attached to the 1, 2, 3, and 6 positions of the D-glucitol molecule

Reactivity

Highly reactive due to the presence of acetyl groups

Applications

Potential use in the pharmaceutical industry for drug development and drug delivery systems

Advantages

Unique structure and reactivity make it a valuable tool in organic chemistry and pharmaceutical product development

Protection

Shields hydroxyl groups from unwanted reactions during organic synthesis

Synthesis

Commonly used in organic synthesis for the protection of hydroxyl groups

Industry

Has potential applications in the pharmaceutical industry for the development of new drugs and drug delivery systems.

Upstream product

• 108-24-7 acetic anhydride 
• 7726-97-8 1,4-anhydro-D-glucitol 
• 51196-40-8 1,4-anhydro-DL-galactitol 
• 488-43-7 1-Amino-1-deoxy-D-glucitol 
• 83823-00-1 C₄₄H₉₄B₈O₁₁ 
• 83823-00-1 C₄₄H₉₄B₈O₁₁ 
• 7726-97-8 1,4-anhydro-D-glucitol 
• 5540-31-8 methyl 3,6-anhydro-α-D-galactopyranoside 

Relevant articles and documents

ACYLATED ACTIVE AGENTS AND METHODS OF THEIR USE FOR THE TREATMENT OF AUTOIMMUNE DISORDERS

Disclosed herein are acylated active agents (e.g., acylated catechin polyphenols, acylated carotenoids, acylated mesalamines, acylated sugars, acylated shikimic acids, acylated ellagic acid, acylated ellagic acid analogue, and acylated hydroxybenzoic acids), active agent combinations (e.g., with a second agent that is a fatty acid) and methods of their use, e.g., for modulating an autoimmunity marker or for treating an autoimmune disorder.

MULTIBIOTIC AGENTS AND METHODS OF USING THE SAME

Multibiotic agents are disclosed. The multibiotic agents may contain two or more moieties linked through bonds cleavable in vivo. The bonds cleavable in vivo can be ester bonds, amide bonds, azo bonds, glycosidic bonds, carbonate linkers, or carbamate linkers. The moieties can be alcohol cores, amine cores, and/or acyls. Also disclosed are compositions containing multibiotic agents and methods of using the multibiotic agents.

An Efficient Synthesis of Anhydroalditols and Allyl C-Glycosides

Efforts to expedite production of anhydroalditols have led to a new, efficient synthesis of these compounds from alkyl glycosides.Silylation of the glycoside followed by reductive cleavage in the presence of triethylsilane and trimethylsilyl trifluoromethanesulfonate were carried out in the same reaction flask.Subsequent aqueous workup gave excellent yields of anhydroalditol(s).In some cases ring contraction was observed, but the use of bulkier silyl protecting groups gave greater yields of the expected product.This method was also shown to be an efficient means to prepare allyl C-glycosides, without any independent protecting or activating step, by simply replacing triethylsilane with allyltrimethylsilane in the synthetic scheme.