1008750-57-9

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 808761-99-1 phenyl 4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside 

Downstream Products

• 1227636-76-1 phenyl 2-O-allyl-3-O-(p-methoxybenzyl)-4,6-O-(p-methoxybenzylidene)-1-thio-α-D-mannopyranoside 
• 1008750-58-0 phenyl 3-O-p-methoxybenzyl-4,6-O-p-methoxybenzylidene-2-O-benzyl-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

Stereoselective total synthesis of acremomannolipin A and its anomer, the potent calcium signal modulators with a novel glycolipid structure: Role of the stereochemistry at the anomeric center on the activity

A full account of stereoselective total synthesis of a novel glycolipid, acremomannolipin A (1), the potent calcium signal modulator isolated from Acremonium strictum, by employing the stereoselective β-mannosylation of 4,6-O-benzylidene-protected mannosy

Structure-Activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 4: Role of acyl side chains on d-mannose

As part of an ongoing study on the structure-Activity relationship of acremomannolipin A (1)-the novel glycolipid isolated from Acremonium strictum possessing potent calcium signal-modulating activity-the role of acyl substituents on the d-mannose moiety was examined. Three partially deacylated homologs (2a-2c) and 20 homologs (2d-2w) bearing different acyloxy side chains were synthesized via the stereoselective β-mannosylation of appropriately protected mannosyl sulfoxides (3) with d-mannitol derivatives (4), and their calcium signal-modulating activities were examined. The activities of 2a-2c were completely lost. Homologs bearing relatively short acyloxy groups at C-3, C-4, and C-6 positions (2t-2v) exhibited less activity than 1, whereas a heptanoyl homolog (2w: C7) maintained activity nearly equal to that of 1. When the acyl groups at these three positions were substituted by an octanoyl group (2i: C8), the activity was completely lost. On the other hand, of the 10 homologs in which the octanoyl at C-2 was substituted by other acyloxy moieties (2j-2s), three (2m: C7, 2n: C9, 2o: C10) maintained potent activity. These results suggested that peracylated mannose structure is critical for calcium signal-modulating activity, and this activity is precisely dependent on the length of four acyl side chains on d-mannose.

Synthesis of a glycosylphosphatidylinositol anchor bearing unsaturated lipid chains

A GPI anchor bearing unsaturated fatty acid lipid chains (1) was synthesized by a highly convergent strategy employing the para-methoxybenzyl group for permanent hydroxyl protection. The final global deprotection was achieved by an efficient three-step, one-pot procedure to give an 81% isolated yield of the target structure.