28154-37-2

Basic information

• Product Name: β-D-Mannopyranose 1,2,3,4-tetraacetate
• Synonyms: β-D-Mannopyranose 1,2,3,4-tetraacetate
• CAS NO: 28154-37-2
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.3026
• Mol File: 28154-37-2.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: β-D-Mannopyranose 1,2,3,4-tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: β-D-Mannopyranose 1,2,3,4-tetraacetate(28154-37-2)
• EPA Substance Registry System: β-D-Mannopyranose 1,2,3,4-tetraacetate(28154-37-2)

Safety Data

• Hazardous Substances Data: 28154-37-2(Hazardous Substances Data)

Usage

General Description

β-D-Mannopyranose 1,2,3,4-tetraacetate is a chemical compound that is a derivative of the sugar mannose. It consists of a mannose molecule that has been modified with four acetyl groups, one on each of its carbon atoms. β-D-Mannopyranose 1,2,3,4-tetraacetate is commonly used in organic synthesis and as a starting material for the production of other compounds. It has applications in the pharmaceutical and food industries, where it can be used as a building block for the synthesis of various drugs and as a flavoring agent in certain food products.β-D-Mannopyranose 1,2,3,4-tetraacetate is also used in research as a model compound for studying the reactivity and structure of carbohydrate derivatives. Overall, this compound plays a significant role in various scientific and industrial applications due to its unique chemical properties and reactivity.

Upstream product

• 10028-44-1 1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-α-D-glucopyranose 
• 604-68-2 α-D-glucopyranose peracetylate 
• 83-87-4 D-glucose pentaacetate 
• 71208-20-3 1,2,3,4-tetra-O-acetyl-6-O-benzoyl-α-D-glucopyranose 
• 67919-36-2 1,2,3,4-tetra-O-acetyl-6-O-trityl-D-glucopyranoside 
• 492-62-6 alpha-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 54325-28-9 (2R,3R,4S,5S,6R)-6-Trityloxymethyl-tetrahydro-pyran-2,3,4,5-tetraol 
• 54325-28-9 6-O-trityl-α-D-glucose 
• 2280-44-6 D-Glucose 

Downstream Products

• 108321-48-8 1,2,3,4-tetra-O-acetyl-6-O-<(diphenoxy)phosphoryl>-β-D-mannopyranose 
• 87303-54-6 1,2,3,4-Tetra-O-acetyl-6-O-(p-tolylsulfonyl)-β-D-mannopyranose 
• 129785-40-6 1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-β-D-mannopyranose 
• 108257-52-9 1,2,3,4-tetra-O-acetyl-6-O-benzyl-α-D-glucopyranose 
• 176040-66-7 phenyl 2,3,4-tri-O-acetyl-1-thio-α-D-mannopyranoside 
• 71208-20-3 1,2,3,4-tetra-O-acetyl-6-O-benzoyl-α-D-glucopyranose 
• 129728-68-3 4-nitrophenyl 4,6-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 129728-69-4 4-nitrophenyl 4,6-di-O-acetyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 129728-65-0 4-nitrophenyl 4-O-acetyl-6-deoxy-6-fluoro-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 129728-66-1 4-nitrophenyl 4-O-acetyl-6-deoxy-6-fluoro-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 1034191-98-4 C₂₁H₂₃NO₁₄ 

Relevant articles and documents

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Regio- A nd chemoselective deprotection of primary acetates by zirconium hydrides

A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.

Total synthesis of agalloside, isolated from: Aquilaria agallocha, by the 5-O-glycosylation of flavan

Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.