98021-64-8

Basic information

• Product Name: Arabinuronic acid, gamma-lactone (6CI,9CI)
• Synonyms: Arabinuronic acid, gamma-lactone (6CI,9CI)
• CAS NO: 98021-64-8
• Molecular Formula: C5H6O5
• Molecular Weight: 146.09814
• Product Categories: ALDEHYDE
• Mol File: 98021-64-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Arabinuronic acid, gamma-lactone (6CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Arabinuronic acid, gamma-lactone (6CI,9CI)(98021-64-8)
• EPA Substance Registry System: Arabinuronic acid, gamma-lactone (6CI,9CI)(98021-64-8)

Safety Data

• Hazardous Substances Data: 98021-64-8(Hazardous Substances Data)

Upstream product

• 63-29-6 D-glucurono-6,3-lactone 

Downstream Products

• 1389271-11-7 methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1-methanesulfonyloxy-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate 
• 1389271-02-6 C₂₄H₃₅NO₁₁S₃Si 
• 1389271-16-2 methyl 2-[(1R,2R,3S)-3-(benzyloxycarbonyl)-1-methanesulfonyloxy-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate 
• 1403601-11-5 C₂₄H₃₅NO₁₁S₃Si 

Relevant articles and documents

Stereoselective synthesis of highly functionalized thiopeptide thiazole fragments from uronic acid/cysteine condensation products: Access to the core dipeptide of the thiazomycins and nocathiacins

We present the stereoselective synthesis of various highly functionalized thiazole dipeptides that are found in thiopeptide antibiotics like thiazomycins and nocathiacins. The condensation of an uronic acid with l-cysteine methyl ester delivers along two different protocols the stereopure thiazolidine lactones or lactams on the multigram scale, respectively. Oxidation of the thiazolidine moiety to the thiazole and tailoring of the sugar chains yield the thiazole dipeptide as present in the core motif of the thiopeptide antibiotics, as well as its epimer and a homolog. The modular assembly of the potent natural products and their analogs relies on the synthetic accessibility of adequately protected building blocks of tailored absolute stereochemistry.

Side-chain-functionalized dipeptides derived from 6,5-fused bicyclic thiazolidinlactams

Condensation of D-arabinuronolactone (2) with L-cysteine methyl ester yields the bicyclic thiazolidinlactam 3 as a single diastereoisomer with the new bridgehead stereocenter in the (S) configuration. Regioselective activation of the a-hydroxy group leads to the triflate 4 without requiring protecting groups on the residual hydroxy groups. Subsequent azide exchange, reduction, and Boc protection, yields the epimeric dipeptide mimetics 6 and 7. Compound 3 forms the single acetonide 9, which permits the regioselective alkylation of the γ-hydroxy group of the bicyclic framework. Subsequent deprotection and exchange of the α-hydroxy functionality against a Boc-protected amino group (13) demonstrates the regioselective side-chain modification of bicyclic dipeptides. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.