Synthesis of N-unsubstituted, mono- and disubstituted carbohydrate-1-O-carbamates and their behaviour in glycoside syntheses

Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry

“…A representative example shown in Table 5 makes use of an N -trichloroacetyl carbamate leaving group introduced by Redlich 96 and Vankar. 97 Omura et al .…”

Chemical Modification of the N Termini of Unprotected Peptides for Semisynthesis of Modified Proteins by Utilizing a Hydrophilic Protecting Group

“…However, for the partial protection of peptides we need suitably activated carbohydrates. Carbamate is the preferable form for amine protection; we chose imidazole‐activated carbohydrates and synthesized AGlOC‐imidazole 1 …”

“…Carbamate is the preferable form fora mine protection;w ec hose imidazole-activated carbohydrates and synthesized AGlOC-imidazole 1. [20] To investigate the optimal conditions for partial protection, we synthesized as hort modelp eptide 2,w hichi sapart of in-terleukin-8, by 9-fluorenylmethoxycarbonyl-solid-phase peptide synthesis (Fmoc-SPPS). Ta ble 1s hows the conditions for the protection of peptide 2.W ef ound that additives such as N-hydroxysuccinimide (HOSu) or 1-hydroxybenzotriazole (HOBt) are essential for efficient protection.…”

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

“…195,255 More recently, the Mong group suggested that in addition to the anomeric effect the formation of 1,2-cis nitrilium species is further reinforced by the participation of the oxygen atom at C-2. 256 This would result in the formation of the glycosyl oxazolinium intermediate that is leading to the β -product as a result of the top-face nucleophilic attack (see refs 255, 257–262, 254, 256, 261, 254, 256–261, 254, 256–261, 253, 255–260, 253, 255–260, 252, 254–259).…”

“…Conversely, nitrile solvents help the formation of β-glycosides because these reactions were thought to proceed via the axial glycosyl nitrilium cation intermediate. , More recently, the Mong group suggested that in addition to the anomeric effect the formation of 1,2-cis nitrilium species is further reinforced by the participation of the oxygen atom at C-2 . This would result in the formation of the glycosyl oxazolinium intermediate that is leading to the β-product as a result of the top-face nucleophilic attack (see refs , − , , , , , − , , − , , − , , − , , − ).…”