183875-02-7

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 202462-37-1 phenyl 2-azido-2-deoxy-1-thio-α/β-D-glucopyranoside 
• 108-98-5 thiophenol 
• 183875-22-1 phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside 
• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 
• 183875-35-6 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-1-thiol-α-D-glucopyranoside 

Downstream Products

• 183875-13-0 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-((2R,4aR,6R,7R,8R,8aS)-7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 183875-05-0 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-((2R,4aR,6R,7R,8R,8aS)-7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 277756-85-1 phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside 
• 325480-28-2 (R)-2-((2R,4aR,6R,7R,8R,8aS)-7-Azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 
• 325480-31-7 C₄₆H₆₀F₃N₉O₁₄S 
• 154920-28-2 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate 
• 220688-23-3 phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside 
• 310870-37-2 O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate 
• 277756-88-4 phenyl 2-azido-3,6-di-O-benzyl-4-O-(tert-butyldimethylsilyl)-2-deoxy-1-thio-α-D-glucopyranoside 
• 176106-81-3 Galβ1-4(Fucα1-3)GlcNAcβ1-OMe 
• 183875-24-3 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6R)-3-azido-5-hydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-3-yl ester 
• 183875-32-3 C₃₉H₄₃N₃O₉S 
• 183875-23-2 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6R,7R,8R,8aS)-7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester 
• 183875-06-1 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 

Relevant academic research and scientific papers

Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from d -Glucosamine

An improved and scalable synthesis of orthogonally protected d-glucosamine and d-galactosamine building blocks from inexpensive d-glucosamine has been developed. The key reaction is an inversion/migration step providing access to a fully orthogonal protec

Conformational Lock of Glycosyl Donors Using Cyclic Carbamates

Axial rich glycosyl donors often display superior reactivity and stereoselectivity in glycosylations. In this study, a glucosamine glycosyl donor, locked in a 1C4 conformation by a six-membered carbamate ring, i.e. an oxazinone, is synthesized and studied. The 2N,4O carbamate is synthesized in one step from the corresponding azide. The glycosylation properties were studied by glycosylating different alcohols. Derivatives of the glycosyl donor were synthesized by introducing Ac, Troc, Ts, and Ms groups on the oxazinone nitrogen. The ring opening to give the glycoside in the 4C1 conformation was found to proceed smoothly using Zemplén conditions.

Synthesis and biological evaluation of analogues of bacterial lipid I

Bacterial Lipid I analogues containing different anomeric groups at the muramic acid moiety were synthesized and screened in MurG enzyme assays run in the presence and absence of cell wall membranes. The results obtained in this study help elucidate the role of the lipid diphosphate in the recognition of Lipid I by MurG. (C) 2000 Elsevier Science Ltd.

Generalizing glycosylation: Synthesis of the blood group antigens Lea, Leb, and Le(x) using a standard set of reaction conditions

Because there are no general reaction conditions for any glycosylation method, biologically interesting oligosaccharides can only be made in a small number of laboratories in the world. To make carbohydrate synthesis accessible to nonspecialists, it is critical to have glycosylation methods that will work in a wide range of cases under a single set of conditions. The Lewis blood group antigens have attracted the attention of numerous synthetic carbohydrate groups because of their structural complexity. Although they have been synthesized many times, they have never been made using a single glycosylation method under one set of reaction conditions. In this paper, we show that the sulfoxide glycosylation method can be used to form all of the glycosidic linkages in the Lewis blood group antigens Lea (1), Leb (2), and Le(x) (3) stereoselectively under a uniform set of reaction conditions. This work highlights the flexibility of the sulfoxide method and demonstrates its utility for constructing families of related oligosaccharides.