179072-68-5

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 179072-63-0 phenyl 3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 
• 71676-30-7 phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 824-94-2 p-methoxybenzyl chloride 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 

Downstream Products

• 256413-56-6 tert-Butyl-[(2S,4aR,6S,7R,8S,8aS)-8-(4-methoxy-benzyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-dimethyl-silane 
• 403646-42-4 S-phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-2-O-pivaloyl-1-thio-β-D-galactopyranoside 
• 179072-60-7 C₆₈H₇₉NO₂₀ 
• 179072-57-2 4-Oxo-pentanoic acid (2S,4aR,6S,7R,8S,8aR)-8-hydroxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 179072-59-4 C₇₃H₈₅NO₂₂ 
• 179072-58-3 C₇₁H₇₃NO₂₁S 
• 256413-36-2 7-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 256413-39-5 toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl ester 
• 256413-42-0 (2S,3S,4S,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-4-ol 
• 256413-38-4 (2R,4aR,6S,7S,8S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 
• 256413-37-3 (2R,4aR,6S,7S,8S,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 
• 306747-66-0 (2R,4aR,6S,7R,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 
• 256413-32-8 Toluene-4-sulfonic acid (2R,3S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 306747-67-1 Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Total synthesis of everninomicin 13,384-1 - Part 3: Synthesis of the DE fragment and completion of the total synthesis

The stereoselective construction of the DE fragment (2) of everninomicin 13,384-1 (1) is reported. From the two possible ways of inserting the DE fragment between the A1B(A)C and FGHA2 domains of the natural product, the sequence involving the DEFGHA2 segment was found to be the most viable. This coupling was followed by attachment of a suitably protected and activated A1B(A)C fragment which led, after orthoester construction and final deprotection to the targeted everninomicin 13,384-1 (1), completing the total synthesis of this complex naturally occurring substance.

Orthogonal glycosylation strategy in synthesis of extended blood group B determinant

The orthogonal glycosylation strategy was applied for the synthesis of extended blood type B determinant (2) of a novel glycolipid 1. Key features in the synthesis are 1) four monosaccharide units were synthesized as either glycosyl fluoride or thioglycoside to be engaged to the orthogonal glycosylation strategy and 2) all necessary manipulations were completed at the monosaccharide level, therefore, manipulations during the elongation of sugar chain were minimized.