61329-67-7

Upstream product

• 108-24-7 acetic anhydride 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1223405-99-9 methyl 4-O-acetyl-2,3-di-O-benzyl-6-O-(2-nitro)phenylacetyl-α-D-glucopyranoside 
• 141-78-6 ethyl acetate 

Downstream Products

• 1223405-99-9 methyl 4-O-acetyl-2,3-di-O-benzyl-6-O-(2-nitro)phenylacetyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

3-Butenyloxycarbonyl as a new hydroxyl protecting group in carbohydrate synthesis

3-Butenyloxycarbonyl (Bloc) has been identified as a new hydroxyl protecting group, which can be introduced under mild conditions in high yields and selectively removed by OsO4/NaIO4/2,6-lutidine in CH3CN-H2O wi

Synthesis of an α-amylase inhibitor: Highly stereoselective glycosidation and regioselective manipulations of hydroxyl groups in carbohydrate derivatives

Here, we describe the efficient synthesis of α-amylase inhibitor 1. To introduce the most expensive C ring unit at a late stage in the synthesis, we developed 1,2-cis-O-glycosidation of AB and C ring intermediates. Taking advantage of the effect of non-neighboring protecting groups, reaction solvents, and temperature for the glycosidation led to high stereoselectivity and high yield of the 1,2-cis-glycoside product bearing the API skeleton. We also explored protection and deprotection methods for regioselective manipulation of hydroxyl groups in A and B ring intermediates. One-pot benzylation of the 2,3-hydroxyl groups of d-glucose under phase-transfer conditions and regioselective anomeric deacetylation with N-methylpiperazine were developed for the syntheses of A, B, and AB ring intermediates. Thus, the efficiency of the process was dramatically improved. The raw material cost of API was reduced to approximately one-third that of the original route, and the total process was decreased by six steps.

Monoacetylation of carbohydrate diols via transesterification with ethyl acetate

Monoacetylation of secondary diols in protected monosaccharides was achieved with ethyl acetate as acyl donor and sodium tert-butoxide as a base. The regioseletivity of the reaction varied depending on the substrate. This new method provides a simple, fast, and efficient method to access selectively acetylated carbohydrates that is compatible with acid-sensitive protecting groups. CSIRO 2014.

(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.

A simple one-pot method for the synthesis of partially protected mono- and disaccharide building blocks using an orthoesterification-benzylation-orthoester rearrangement approach

A simple one-pot method is reported for making partially protected glycosyl acceptors from O-methyl or S-alkyl/aryl glycosides of D-glucose, D-galactose, D-arabinose, L-rhamnose, L-fucose and lactose via orthoester formation, benzylation and selective hydrolysis.

Regioselective alkylation and acylation of carbohydrates engaged in metal complexes.

Substituted carbohydrate derivatives (D-gluco, D-manno, and D-galacto) having two free hydroxyl groups were converted into their metal chelates by reaction with sodium hydride and a metal chloride (cupric or mercuric) in either oxolane or 1,2-dimethoxyeth