151992-85-7

Upstream product

• 151992-84-6 ethyl 2-O-benzoyl-3-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 1223405-93-3 methyl 2,3,4-tri-O-benzyl-6-O-(2-nitro)phenylacetyl-α-D-glucopyranoside 
• 151992-83-5 ethyl 3-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 98-88-4 benzoyl chloride 

Downstream Products

• 151992-86-8 tert-butyl (ethyl 2-O-benzoyl-3-O-benzyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranosid)uronate 
• 151992-88-0 methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside 
• 151992-87-9 methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside 
• 1223406-00-5 ethyl 2-O-benzoyl-3-O-benzyl-4-O-(4-methoxybenzyl)-6-O-(2-nitro)phenylacetyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

(2-Nitrophenyl)acetyl: A new, selectively removable hydroxyl protecting group

Figure presented The utility of the (2-nitrophenyl)acetyl (NPAc) group for the protection of hydroxyl functions is reported. (2-Nitrophenyl)acetates are readily prepared starting from the commercially available, inexpensive (2-nitrophenyl)acetic acid, and these esters are stable under a series of common carbohydrate transformations. The NPAc group can be removed selectively using Zn and NH4Cl without affecting a series of common protecting groups. This new protecting group is orthogonal with the commonly used tert-butyldimethylsilyl, levulinoyl, 9-fluorenylmethoxycarbonyl, naphthylmethyl, and p-methoxybenzyl groups.

Regio- and chemoselective reductive cleavage of 4,6-O-benzylidene-type acetals of hexopyranosides using BH3·THF-TMSOTf

Benzylidene-type cyclic acetals of carbohydrates undergo efficient reductive ring opening using BH3·THF and a catalytic amount of TMSOTf at room temperature. 4,6-O-Benzylidene-hexopyranosides afford the corresponding 4-O-benzyl ethers exclusive

Synthesis of the methyl glycosides of a tri- and a tetra-saccharide related to heparin and heparan sulphate

The methyl glycoside of a tetrasaccharide isolated from heparin, methyl O-(α-L-idopyranosyluronic acid)-(1 → 4)-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1 → 4)-O-(β-D-glucopyranosyluronic acid)-(1 → 3)-O-β-D-galactopyranoside disodium salt and a trisaccharide derivative thereof, methyl O-(α-L-idopyranosyluronic acid)-(1 → 4)-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1 → 4)-O-β-D-glucopyranosyluronic acid disodium salt, were synthesized using a block-type strategy. A suitable protected disaccharide block of iduronic acid and glucosamine (IdoA-GlcN) was used as a key intermediate for the syntheses and was glycosidated with a protected galactose derivative and a disaccharide block of glucuronic acid and galactose (GlcA-Gal) to give tri- and tetra-saccharide derivatives, respectively. Deprotection gave the target compounds. The methyl glycoside of a tetrasaccharide isolated from heparin, disodium salt and a trisaccharide derivative thereof, were synthesized using a block-type strategy. A suitable protected disaccharide block of iduronic acid and glucosamine (IdoA-GlcN) was used as a key intermediate for the syntheses and was glycosidated with a protected galactose derivative and a disaccharide block of glucuronic acid and galactose (GlcA-Gal) to give tri-and tetra-saccharide derivatives, respectively. Deprotection gave the target compounds.