496812-01-2

Upstream product

• 138566-31-1 Acetic acid (2R,3S,4S,5R,6R)-6-acetoxymethyl-4,5-bis-benzyloxy-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester 
• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 65827-57-8 1,2,6-tri-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranose 

Downstream Products

• 138566-32-2 ethyl 2,6-di-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 496812-18-1 ethyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside 
• 138566-38-8 Diisopropyl-phosphoramidous acid benzyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 138566-36-6 (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-3-ol 
• 138566-33-3 C₆₂H₆₂O₁₃ 
• 138566-34-4 (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3-ol 
• 496812-03-4 ethyl 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 
• 496812-19-2 ethyl 3,4-di-O-benzyl-2-O-p-methoxybenzyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 
• 496812-02-3 ethyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 
• 496812-04-5 ethyl 6-O-allyl-3,4-di-O-benzyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 
• 496812-20-5 ethyl 3,4-di-O-benzyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

SmI2/water/amine mediates cleavage of allyl ether protected alcohols: application in carbohydrate synthesis and mechanistic considerations.

[reaction: see text]. SmI2/H2O/amine provides selective cleavage of unsubstituted allyl ethers in good to excellent yields. This method is therefore useful in deprotection of alcohols and carbohydrates.

SYNTHESIS OF A PEPTIDYLDIMANNOSYL PHOSPHATE: FRAGMENT OF THE VARIANT-SPECIFIC SURFACE GLYCOPROTEIN MEMBRANE ANCHOR FROM TRYPANOSOMA BRUCEI

Condensation of protected β-benzyl-aspartate 4 with 2-amino-ethanol, subsequent deprotection of the amino function and coupling with N,N'-di-benzyloxycarbonyl-lysine (7) afforded the peptidyl alcohol 8.Glycosylation of methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (11) by ethyl 2,6-di-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside (14) gave, after debenzoylation and protection of the 2'-hydroxyl function, the suitably protected dimannoside 21.Phosphitylation of 21 with benzyloxy-bis-(N,N-diisopropylamino)phosphine (18) followed by the addition of 8 gave, after oxidation and subsequent hydrogenolysis of the benzyl groups, the title compound in a good yield.