137172-47-5

Upstream product

• 100-39-0 benzyl bromide 
• 20746-64-9 allyl (R)-4,6-O-benzylidene-β-D-gluco-pyranoside 
• 1223406-14-1 allyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2-nitro)phenylacetyl-β-D-glucopyranoside 
• 259882-15-0 allyl 4,6-O-benzylidene-D-glucopyranoside 
• 119111-33-0 (3aS,5aR,8R,9aR,9bS)-4-Allyloxy-2,8-diphenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 214490-84-3 Allyl 2,3,4,6-Tetra-O-acetyl-D-mannopyranoside 
• 182212-07-3 α,β-O-allyl-D-mannopyranoside 

Downstream Products

• 137105-33-0 N-[4-((2R,4aR,6R,7R,8S,8aR)-6-Allyloxy-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxymethyl)-phenyl]-2,2-dimethyl-propionamide 
• 534575-33-2 allyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside 
• 1223406-14-1 allyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2-nitro)phenylacetyl-β-D-glucopyranoside 
• 1443672-41-0 allyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside 
• 1443672-42-1 allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-β-D-glucopyranoside 
• 1443672-43-2 allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside 
• 1443672-40-9 allyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 

Relevant academic research and scientific papers

n-Propyl 6-amino-2,6-dideoxy-2,2-difluoro-β-d-glucopyranoside is a good inhibitor for the β-galactosidase from E. coli

A convenient route has been developed for the synthesis of novel 6-amino-2,2-(or 3,3-difluoro)-2-(or 3),6-dideoxy-hexopyranoses. Biological screening showed these compounds as good inhibitors for several glycosidases. Especially n-propyl 6-amino-2,6-dideoxy-2,2-difluoro-β-d-glucopyranoside (8) was an excellent competitive inhibitor for the β-galactosidase from E. coli holding a Ki of 0.50 μM. [Figure not available: see fulltext.]

Protecting Group Dependence of Stereochemical Outcome of Glycosylation of 2-O-(Thiophen-2-yl)methyl Ether Protected Glycosyl Donors

A series of glycosyl donors possessing a (thiophen-2-yl)methyl ether protecting group at position 2 were synthesised and the effect of the protecting group pattern of other hydroxyls on the stereochemical outcome of glycosylation was investigated. Studies revealed optimal α-selectivity for glycosylation using a fully armed tri-benzylated donor, whilst other protecting group patterns were significantly less effective. Low-temperature NMR studies of both fully armed and fully disarmed donors revealed the intermediacy of cyclised sulfonium ion intermediates. Reaction conditions were developed which allowed removal of the (thiophen-2-yl)methyl ether protecting group either selectively, or together with benzyl ethers. Glycosyl donors with a 2-O-thiophenylmethyl ether protecting group undergo six-membered ring NGP, as demonstrated by low-T NMR studies, but the stereochemical outcome of glycosylation is highly dependent on other protecting groups.

(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.

Total synthesis of 3,3-difluorinated 1-deoxynojirimycin analogues

Difluorination of 1-deoxynojirimycin at position C(3) creates a competitive inhibitor 15 of 10 times higher activity against an α-glucosidase than the parent compound. Its screening against a panel of human cell lines showed a low cytotoxicity therefore m

Stereochemical Control in Hex-5-enyl Radical Cyclizations: From Carbohydrates to Carbocycles. 3

The hex-5-enyl radical cyclization reaction was applied to prepare highly oxygenated cyclopentanoids from aldopyranose sugars.The Wittig reaction of the sugars readily provides hex-5-en-1-ols which were converted to hex-5-enyl radicals via one of the vari