180782-81-4

Basic information

• Product Name: (S)-1-(hydroxycarbonyl)pentadec-10-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside 1,3-(B)-lactone
• Synonyms: (S)-1-(hydroxycarbonyl)pentadec-10-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside 1,3-(B)-lactone
• CAS NO: 180782-81-4
• Molecular Weight: 690.872
• Mol File: 180782-81-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-1-(hydroxycarbonyl)pentadec-10-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside 1,3-(B)-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(hydroxycarbonyl)pentadec-10-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside 1,3-(B)-lactone(180782-81-4)
• EPA Substance Registry System: (S)-1-(hydroxycarbonyl)pentadec-10-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside 1,3-(B)-lactone(180782-81-4)

Safety Data

• Hazardous Substances Data: 180782-81-4(Hazardous Substances Data)

Upstream product

• 7404-35-5 1,2,3,4-tetra-O-acetyl-6-deoxy-α-D-galactopyranose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 197915-84-7 3,4-O-isopropylidene-2-O-pivaloyl-α-D-fucopyranose 
• 197853-45-5 1-(methoxycarbonyl)pentadec-10(S)-yl 2,3,4-tri-O-acetyl-β-D-fucopyranoside 
• 197853-38-6 ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 197853-43-3 1-(tert-butyldimethylsiloxy)-11(S)-hexadecanyl acetate 
• 197853-44-4 11(S)-acetoxy-1-hexadecanoic acid 
• 197853-42-2 1-(tert-butyldimethylsiloxy)-11(S)-hexadecanol 
• 180980-45-4 acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside 
• 180782-75-6 1-(methoxycarbonyl)pentadec-10(S)-yl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside 
• 180782-72-3 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranose 1-trichloroacetimidate 
• 180782-60-9 methyl (11S)-11-[(3,4-O-isopropylidene-2-O-pivaloyl-β-D-fucopyranosyl)oxy]hexadecanoate 

Downstream Products

• 197853-54-6 (11S)-11-[[(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-[2,4-di-O-[(2S)-2-methylbutyryl]-α-L-rhamnopyranosyl]-(1->2)-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoic acid 3_glu-lactone 

Relevant articles and documents

Total synthesis of tricolorin A

Tricolorin A (1), a structurally amazing resin glycoside with promising bioactivities from Ipomoea tricolor cav. (convolvulaceae), was synthesized in a total of 45 steps, with the longest linear sequence of 20 steps and overall yield of 0.65% from D-mannitol. The AB disscharide 19-membered lactone 2 was constructured by a regioselective macrolactonization using Corey-Nicolaou protocol. The macrolactone tetrasaccharide 33 was realized either by 'one- pot two-step' glycosylation procedure or by a stepwise assembly employing the 'armed-disarmed' glycosylation strategy.

The First Total Synthesis of Tricolorin A

Keywords: glycosylations; macrocycles; one-pot reactions; total synthesis; tricolorin A