450370-39-5

Upstream product

• 213675-13-9 3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)propanol 
• 82659-55-0 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene 
• 80401-11-2 <1-(acetyloxy)-2-propenyl>trimethylsilane 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 
• 201279-58-5 1-deoxy-1-allyl-2,3,4,6-tetra-O-acetyl-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 100-39-0 benzyl bromide 
• 133697-14-0 2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enitol 

Downstream Products

• 213675-17-3 (E)-5-((2R,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pent-2-enoic acid ethyl 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 
• 912344-29-7 (E)-4-(tetra-O-benzyl-α-D-galactopyranosyl)-1-(thiazol-2-yl)but-2-en-1-one 
• 906651-94-3 (R,E)-2-methyl-N-(3-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)propylidene)propane-2-sulfinamide 
• 912344-33-3 methyl (S)-2-phenyl-2-({(2R,4R)-4-[(tetra-O-benzyl-α-D-glucopyranosyl)methyl]-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran-2-yl}oxy)acetate 
• 912344-38-8 methyl (R)-2-phenyl-2-({(2S,4S)-4-[(tetra-O-benzyl-α-D-glucopyranosyl)methyl]-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran-2-yl}oxy)acetate 
• 1418180-96-7 (2R,3R,4R,5R,6R)-2-((3S,4S,55)-3-(4-(4-(dodecyloxy)phenyl)thiazol-2-ylamino)-4,5-dihydroxynonadecyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1418180-93-4 1-((3S,4S,5S)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-yl)thiourea 
• 1418181-05-1 1-((3S,4S,5R)-4,5-dihydroxy-1-((2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-yl)-3-(4-phenylbutyl)urea 
• 1418180-94-5 5-(biphenyl-4-yl)-N-((3S,4S,5R)-4,5-dihydroxy-1-((2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-yl)pentanamide 
• 906652-15-1 tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate 
• 906652-17-3 tert-butyl (3S,4R,5S)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate 
• 1063630-35-2 5-(3,4,5-tris(benzyloxy)-6-benzyloxymethyl-tetrahydropyran-2-yl)pent-2-enoic acid methyl ester 
• 213675-21-9 (S)-4-Isopropyl-3-[5-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoyl]-oxazolidin-2-one 

Relevant academic research and scientific papers

Expedient synthesis of the α-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000)

Key reactions in a concise synthesis of an α-C-galactosylceramide analogue of KRN7000 include a diastereoselective alkenylalane addition to an N-tert-butanesulfinyl imine and the use of an epoxidation/carbamate ring opening sequence to install the aminodi

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

Design and synthesis of a novel class of sugar-peptide hybrids: C-linked glyco β-amino acids through a stereoselective "acetate" Mannich reaction as the key strategic element

A new type of sugar-amino acid hybrid, which is comprised of a sugar unit (gluco-, galacto-, or mannopyranose) linked through a C-glycosidic linkage to the β-position of an α-unsubstituted β-amino acid unit, is presented. It is hypothesized that these new compounds, or the oligomeric peptides derived therefrom, might possess the structural features of β-amino acid oligomers and the chemical and enzymatic resistance of C-glycosides to hydrolysis. The synthetic strategy is based on a new Mannich-type reaction between a chiral acetate enolate equivalent and α-amido sulfones derived from the corresponding sugar-C-glycoside aldehydes. While the sugar-C-glycoside aldehyde partner is prepared from well-established transformations on known sugar precursors, the lithium enolate derived from (1 R)-endo-2-acetylisoborneol 3 is employed as the key element. This Mannich approach proceeds with essentially perfect diasteromeric control leading to the new β-amino carbonyl adducts in good yields. Further, cleavage of the camphor auxiliary is smoothly performed by oxidative treatment with ammonium cerium nitrate (CAN). Complementarily, direct peptide-type coupling of the β-amino carbonyl Mannich adducts with an α- or β-amino acid residue and subsequent CAN-promoted detachment of the auxiliary yields dipeptide fragments bearing a sugar-containing aliphatic side chain and is a process that can be iterated. A preliminary conformational study based on the combination of experimental NMR data and molecular mechanics and molecular dynamics (MD) of one particular adduct is also provided.

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.