60076-41-7

Usage

Uses

Used in Pharmaceutical Industry:
Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside is used as a reagent/reactant for the synthetic preparation of heparin partial structures. Heparin is a highly sulfated glycosaminoglycan with potent anticoagulant properties, making it an essential component in various medical treatments and interventions. Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside's ability to contribute to the synthesis of heparin-like molecules highlights its potential in developing novel therapeutic agents with improved pharmacological properties.
Used in Research and Development:
In the field of glycobiology and carbohydrate chemistry, Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside serves as a valuable intermediate in the synthesis of complex carbohydrate structures. Its unique structural features allow researchers to explore new synthetic routes and develop innovative strategies for the preparation of biologically active compounds, such as glycoconjugates, glycoproteins, and glycolipids.
Used in Diagnostic Applications:
Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside's ability to form heparin partial structures also makes it a potential candidate for diagnostic applications. It can be used to develop assays and tests that measure the binding activities of these structures to human platelets, providing valuable insights into the mechanisms of blood clotting and the effectiveness of heparin-based therapies. This information can be crucial for the development of new diagnostic tools and personalized medicine approaches.

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 4704-15-8 ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 3006-58-4 2-carbobenzyloxyamino-2-deoxy-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 501-53-1 benzyl chloroformate 
• 100-52-7 benzaldehyde 
• 77059-32-6 benzyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate 

Downstream Products

• 68405-74-3 methyl 3-O-acetyl-2-benzyloxycarbonylamino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 123814-45-9 methyl-[O³-benzoyl-O⁴,O⁶-((Ξ)-benzylidene)-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside] 
• 115944-83-7 methyl-[O⁴,O⁶-((Ξ)-benzylidene)-2-benzyloxycarbonylamino-O³-methanesulfonyl-2-deoxy-α-D-glucopyranoside] 
• 60076-40-6 methyl-[O⁴,O⁶-((Ξ)-benzylidene)-2-benzyloxycarbonylamino-O³-(toluene-4-sulfonyl)-2-deoxy-α-D-glucopyranoside] 
• 116607-15-9 methyl-[O⁴,O⁶-((Ξ)-benzylidene)-2-benzyloxycarbonylamino-O³-methyl-2-deoxy-α-D-glucopyranoside] 
• 87907-34-4 methyl 3-O-benzyl-4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 
• 113886-86-5 Acetic acid (2S,5R,6R)-6-((4aR,6S,7R,8R,8aS)-7-benzyloxycarbonylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester 
• 85464-64-8 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((4aR,6S,7R,8R,8aS)-7-benzyloxycarbonylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-4-yl ester 
• 85464-55-7 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((4aR,6S,7R,8R,8aS)-7-benzyloxycarbonylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-4-yl ester 
• 118190-40-2 Benzoic acid (2S,3S,4R,5R,6S)-5-benzyloxycarbonylamino-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 110236-61-8 Methyl-4-O-(2-O-acetyl-3-O-benzyl-α-L-idopyranosyl)-3,6-di-O-benzyl-2-(benzyloxycarbonylamino)-2-desoxy-α-D-glucopyranosid 
• 110236-59-4 Methyl-3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-O-isopropyliden-α-L-idopyranosyl)-2-(benzyloxycarbonylamino)-2-desoxy-α-D-glucopyranosid 
• 110255-42-0 (2R,3S,4S,5R,6R)-5-Acetoxy-4-benzyloxy-6-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 110236-60-7 Acetic acid (4aS,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 

Relevant academic research and scientific papers

PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF

Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and efficient and scalable processes for the industrial scale production of fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions are provided.

Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation

Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd2(dba)3 and Bu3P granted access to a novel series of 3′,4′-dideoxy- 4′,5′-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

Synthesis of heparin partial structures and their binding activities to platelets

A synthetic pentasaccharide corresponding to the antithrombin III-binding region in heparin was also found to bind to human platelets. To identify the platelet-binding site in the pentasaccharide which is expected to be a novel sequence in heparin responsible for its platelet-binding, five partial structures of this particular pentasaccharide were synthesized. In a competitive assay using [3H]-heparin, a trisaccharide, O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-α-D-glucopyranosyl)- (1→4)-O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1→4)-2-deoxy-2-sulfamido-6-O-sulfo-α-D-glucopyranose, was concluded to be a high-affinity site for heparin's binding to platelets.

SYNTHESIS OF CARBOCYCLIC LIGNAN VARIANTS RELATED TO PODOPHYLLOTOXIN

Carbocyclic lignan variants related to podophyllotoxin were synthesized by a stereoselective BF3-catalyzed coupling of podophyllotoxin derivative with chiral aminocyclitols.