197853-38-6

Upstream product

• 108-24-7 acetic anhydride 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 75-36-5 acetyl chloride 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 

Downstream Products

• 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 
• 180782-78-9 1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside 
• 180782-81-4 (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 
• 197916-04-4 methyl (11S)-11-[[(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate 
• 1237748-37-6 4-methoxyphenyl (2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 23262-88-6 O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O¹,O²-((Ξ)-1-methoxy-ethylidene)-α-D-glucopyranose 
• 1313593-72-4 C₂₅H₂₆O₉ 
• 1313593-73-5 C₂₀H₂₄O₉ 
• 1313593-74-6 C₂₇H₂₆Cl₃NO₉ 
• 1313593-75-7 C₂₂H₂₄Cl₃NO₉ 
• 1313593-76-8 C₁₆H₂₀O₇ 

Relevant academic research and scientific papers

Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups

The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.

Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides displaying a range of anomeric substituents

The regioselective C-3-O-acylation and O-methylation of a range of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides has been studied. Regioselectivity is achieved by forming the copper chelate of the 2,3-diol using either sodium hydride and copper(II) chloride, or copper(II) acetylacetanoate, or copper(II) acetate, prior to introduction of the acylating or methylating agent.

Regioselective C-3-O-acylation and O-alkylation of 4,6-O-benzylidene-β-D-glucopyranoside derivatives displaying a range of anomeric substituents

Regioselective C-3-O-acylation and O-alkylation of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside, phenyl 4,6-O-benzylidene-β-D-glucopyranoside and phenyl 4,6-O-benzylidene-1-seleno-β-D-glucopyranoside is described. Regioselectivity is obtained by first treating the benzylidene diols with sodium hydride and copper (II) chloride to form a THF soluble copper chelate.

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