82659-55-0

Upstream product

• 82598-84-3 2,3,4,6-tetra-O-benzyl-D-galactonolactone 
• 1730-25-2 allylmagnesium bromide 
• 219646-55-6 2-S-(2,3,4,6-Tetra-O-benzyl-α-D-galactopyranosyl)-2-oxo-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 762-72-1 allyl-trimethyl-silane 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 3866-62-4 2,3,4,6-tetrakis-O-(phenylmethyl)-1-O-acetyl-α-D-galactopyranose 
• 117307-18-3 phenyl (2,3,4,6-tetra-O-benzyl)-1-thio-β-D-galactopyranoside S-oxide 
• 53263-18-6 allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 201279-58-5 1-deoxy-1-allyl-2,3,4,6-tetra-O-acetyl-D-galactopyranoside 
• 133697-14-0 2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enitol 
• 147242-49-7 (4-Nitro-phenyl)-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methanone 

Downstream Products

• 96689-97-3 ((2R,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde 
• 213675-13-9 3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)propanol 
• 288629-12-9 2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethyl aldehyde 
• 217314-49-3 (3aR,5R,6S,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran 
• 341013-74-9 C₅₀H₆₂N₂O₇ 
• 618387-41-0 1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-propanol 
• 194410-33-8 3-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)propene 
• 450370-85-1 (S)-3-Benzyloxycarbonylamino-5-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid 
• 450370-56-6 [1-(Toluene-4-sulfonyl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-carbamic acid tert-butyl ester 
• 450370-48-6 [1-(Toluene-4-sulfonyl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-carbamic acid benzyl ester 
• 450370-66-8 {(S)-3-((1R,2R,4R)-2-Hydroxy-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-3-oxo-1-[2-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-propyl}-carbamic acid benzyl ester 
• 271246-09-4 1-(3',4',6'-tri-O-benzyl-α-D-lyxo-hexulopyranosyl)-2-propene 
• 271246-08-3 1-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-2-propene 

Relevant academic research and scientific papers

Mild cu(Otf)2-mediated C-glycosylation with chelation-assisted picolinate as a leaving group

C-Glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were developed. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)2 and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corresponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.

Ultrasound-assisted synthesis of C-glycosides

A significant rate enhancement was observed in the preparation of allyl and allenyl-C-glycosides from glycosyl acetate or methyl O-glycoside precursors when ultrasound irradiation was employed as an energy source. The C-glycosides were obtained in 77-96%

Adaptable synthesis of C-glycosidic multivalent carbohydrates and succinamide-linked derivatization

A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic d-mannose, d-glucose, and d-galactose derivatives with different length C1-linked spacer un

Studies on the stereoselective synthesis of C-allyl glycosides

(Equation Presented) An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford α-allylation products in good to excellent yields, the search for conditions favoring β-selectivity proved less successful.

Novel synthetic C-glycolipids, their synthesis and use to treat infections, cancer and autoimmune diseases

The invention is directed to novel compounds of formulae (I), (II) and (III): wherein X is O or NH; R3 is OH or a monosaccharide and R4 is hydrogen, or R3 is hydrogen and R4 is OH or a monosaccharide; R5 is hydrogen or a monosaccharide; and pharmaceutically acceptable salts or esters thereof. The invention is also directed to the use of the compounds both directly and as immune adjuvants for treating cancer, infectious diseases and autoimmune diseases. The invention is also directed to syntheses of the intermediates which can be used to make these novel compounds.

Stereoselective preparation of precursors of α-C-(1→3)- disaccharides

The stereoselectivity of cycloaddition of sugar-containing substituted 1-(thiazol-2-yl)but-2-en-1-ones 1 and vinyl ethers was studied using the achiral vinyl ether/chiral catalyst as well as the chiral vinyl ether/achiral catalyst combinations. It has bee

Facile preparation of an orthogonally protected, pH-sensitive, bioconjugate linker for therapeutic applications

(Chemical Equation Presented) We describe the facile, three-step synthesis of an orthogonally protected, pH-sensitive linker (8), based on maleic acid, and report its application to the preparation of a pH-sensitive phospholipid (20) for potential use in drug and gene delivery. In addition, we highlight the benefits of our linker over the use of the commercially available cis-aconitic anhydride (4).

Efficient synthesis of α-C-galactosyl ceramide immunostimulants: Use of ethylene-promoted olefin cross-metathesis

(Chemical Equation Presented) Olefin cross-metathesis has been used to prepare α-C-galactosylceramide derivatives. The metathesis process merged vinyl and propenyl glycosides with vinyl derivatives of phytosphingosine. The use of ethylene enhanced the yie

Synthesis of C-glycosides from S-glycosyl phosphorothioates

Treatment of O-benzyl protected S-glucosyl phosphorothioates with 1,3,5-trimethoxybenzene in the presence of iodine or boron trifluoride etherate led to appropriate aryl C-β-D-glucosides. The reaction of O-benzyl and O-acetyl-protected phosphorothioates o

Remote asymmtric induction: Synthesis of C-linked α-galactoserine and homoserine derivatives by electrophilic amination

A high diastereoselectivity (98%) for electrophilic of compound 9 using di-t-butyl azodicarboxyl ester as an electrophile was achieved. A similar reaction with compound 13 having achiral oxazolidinone was studied to examine 1,4-remote asymmetric induction. In the latter, a selectivity of 6.5:1 demonstrated the effect of α-galactosyl moiety, responsible for inducing the induction from the remote site.