124477-07-2

Upstream product

• 126923-31-7 C₁₃H₁₆O₅ 
• 100-39-0 benzyl bromide 
• 87470-72-2 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 124477-10-7 (2S,4aR,6S,7R,8S,8aS)-6-Benzenesulfonyl-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 

Downstream Products

• 1041478-23-2 C₂₀H₂₄O₅ 

Relevant academic research and scientific papers

Synthesis of octahydropyrano[3,2-b]pyrrole-2-carboxylic acid derivatives from d-mannose

Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products aeruginosins. Many compounds in the aeruginosin family exhibit inhibition activities toward serine proteases including thrombin and trypsin. The unique Choi structure is the common feature of this family of oligopeptides and this motif is important for their observed biological activities. To better understand the influence of the stereochemistry of the Choi core structure on the inhibition activities, we have previously synthesized ring-oxygenated variants from glucose. The preparation of octahydro-pyrano[3,2-b]pyrrole 2-carboxylic acids from d-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules.

PREPARATION OF PYRANOID GLYCAL DERIVATIVES FROM PHENYL THIOGLYCOSIDES AND GLYCOSYL PHENYL SULPHONES

Phenyl thioglycopyranosides with various protecting groups (acetal, ether, ester) underwent reductive lithiation at C-1, followed by rapid elimination of the 2-substituent, when treated with lithium naphthalenide in tetrahydrofuran at low temperature.Thus

CONVENIENT SYNTHESES OF SUBSTITUTED PYRANOID GLYCALS FROM THIOPHENYL GLYCOSIDES AND GLYCOSYL PHENYLSULFONES

A series of substituted thiophenyl glycosides and glycosyl phenylsulfones were converted in high yield into glycals after reductive lithiation with lithium naphthalenide, followed by elimination of the substituent at C-2.