13036-15-2

Usage

Chemical structure

A derivative of hexopyranose, a six-carbon sugar molecule, with four acetyl groups attached to the hydroxyl groups at positions 1, 3, 4, and 6.

Synthesis

Obtained by acetylating all four hydroxyl groups on the hexopyranose ring, resulting in a highly acetylated form of the sugar.

Stability

The acetylated form enhances the stability of the compound, making it more suitable for various laboratory and industrial applications.

Solubility

The acetylated form improves the solubility of the compound in organic solvents, facilitating its use in chemical reactions and synthesis processes.

Applications

Often used in organic synthesis and as a building block for the preparation of other sugar derivatives.

Pharmaceutical potential

Studied for its potential pharmaceutical applications, particularly in the development of new drugs and drug delivery systems.

Molecular weight

Approximately 332.3 g/mol (calculated from the molecular formula).

Appearance

Typically a white or off-white crystalline solid.

Reactivity

The acetyl groups can be selectively removed or modified in chemical reactions, allowing for the synthesis of various sugar derivatives with different functional groups.

Upstream product

• 108-24-7 acetic anhydride 
• 192753-82-5 2-O-benzyl-3,4,5,6-di-O-isopropyliclenealdehydo-L-gulose 
• 10300-84-2 2,3,4,6-Tetra-O-acetyl-1-O-nitro-β-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 

Downstream Products

• 112742-35-5 O¹,O³,O⁴,O⁶-Tetraacetyl-O²-benzoyl-β-D-glucopyranose 
• 4627-39-8 1,3,4,6-tetra-O-acetyl-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 1195526-52-3 O¹,O³,O⁴,O⁶-Tetraacetyl-O²-diphenoxyphosphoryl-β-D-glucopyranose 
• 178757-74-9 Acetic acid (2S,3R,4S,5R,6R)-2,5-diacetoxy-6-acetoxymethyl-3-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 110462-36-7 O³,O⁴,O⁶-triacetyl-O²-benzoyl-β-D-glucopyranosyl chloride 
• 910887-20-6 methyl-[O³,O⁴,O⁶-triacetyl-O²-(toluene-4-sulfonyl)-β-D-glucopyranoside] 
• 4631-19-0 3,4,6-tri-O-acetyl-2-O-p-toluenesulfonyl-α-D-glucopyranosyl bromide 
• 18968-05-3 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 26209-93-8 5-acetoxy-2-acetoxymethyl-4H-pyran-4-one 
• 72076-24-5 1,3,4,6-Tetra-O-acetyl-2-O-benzoyl-β-D-erythro-hex-2-enopyranose 
• 178757-76-1 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester 
• 189144-27-2 Acetic acid (2R,3R,4S,5R)-3-acetoxy-2-acetoxymethyl-5-((2R,3R,4S,5R,6R)-3-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-chloro-tetrahydro-pyran-4-yl ester 
• 84814-43-7 1,3,4,6-tetra-O-acetyl-2-O-(N-benzyloxycarbonylglycyl)-β-D-glucopyranose 
• 108257-56-3 1,3,4,6-tetra-O-acetyl-2-O-trityl-β-D-glucopyranose 

Relevant academic research and scientific papers

Glycosyl nitrates in synthesis: Streamlined access to glucopyranose building blocks differentiated at C-2

In an attempt to refine a CAN-mediated synthesis of 1,3,4,6-tetra-O-acetyl-α-d-glucopyranose (2-OH glucose) we unexpectedly discovered that this reaction proceeds via the intermediacy of glycosyl nitrates. Improved mechanistic understanding of this reaction led to the development of a more versatile synthesis of 2-OH glucose from a variety of precursors. Also demonstrated is the conversion of 2-OH glucose into a variety of building blocks differentially protected at C-2, a position that is generally hard to protect regioselectively in the glucopyranose series.

Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars: L-Gulose, L-Idose, and the Disaccharide Subunit of Bleomycin A2

The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation - reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-α-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A2.