104040-11-1

Basic information

• Product Name: 2,3-O,O-dibenzyl-4,5-didehydro-5,6-O,O-ditosyl-L-ascorbic acid
• Synonyms: 2,3-O,O-dibenzyl-4,5-didehydro-5,6-O,O-ditosyl-L-ascorbic acid
• CAS NO: 104040-11-1
• Molecular Weight: 664.754
• Mol File: 104040-11-1.mol

Chemical Properties

• CAS DataBase Reference: 2,3-O,O-dibenzyl-4,5-didehydro-5,6-O,O-ditosyl-L-ascorbic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-O,O-dibenzyl-4,5-didehydro-5,6-O,O-ditosyl-L-ascorbic acid(104040-11-1)
• EPA Substance Registry System: 2,3-O,O-dibenzyl-4,5-didehydro-5,6-O,O-ditosyl-L-ascorbic acid(104040-11-1)

Safety Data

• Hazardous Substances Data: 104040-11-1(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 99663-32-8 (2R)-3,4-dibenzyloxy-2-[(1S)-1,2-dihydroxyethyl]-2H-furan-5-one 
• 2871-84-3 (R)-3,4-bis(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 50-81-7 ascorbic acid 

Downstream Products

• 1617539-75-9 (Z)-2,3-O,O-dibenzyl-6-[4-cyclopropyl-1,2,3-triazole-1-yl]-4,5-didehydro-5,6-dideoxy-L-ascorbic acid 
• 1617539-60-2 (Z)-2,3-O,O-dibenzyl-6-(4-butyl-1,2,3-triazole-1-yl)-4,5-didehydro-5,6-dideoxy-L-ascorbic acid 
• 1617539-77-1 (Z)-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-6-(4-tolyl-1,2,3-triazole-1-yl)-L-ascorbic acid 
• 185675-57-4 (Z)-3,4-bis(benzyloxy)-5-(2-hydroxyethylidene)furan-2(5H)-one 

Relevant articles and documents

Antitumor and antiviral activities of 4-substituted 1,2,3-triazolyl-2,3-dibenzyl-L-ascorbic acid derivatives

Two series of 6-(1,2,3-triazolyl)-2,3-dibenzyl-L-ascorbic acid derivatives with the hydroxyethylene (8a?8u) and ethylidene linkers (10c?10p) were synthesized and evaluated for their antiproliferative activity against seven malignant tumor cell lines and antiviral activity against a broad range of viruses. Conformationally unrestricted spacer between the lactone and 1,2,3-triazole units in 8a?8u series had a profound effect on antitumor activity. Besides, the introduction of a long side chain at C-4 of 1,2,3-triazole that led to the synthesis of decyl-substituted 2,3-dibenzyl-L-ascorbic acid 8m accounted for a selective and potent antiproliferative activity on breast cancer MCF-7 cells cells in the nM range. Further analysis showed that compound 8m strongly enhanced expression of hypoxia inducible transcription factor 1 α (HIF-1α) and to some extent decreased expression of nitric oxide synthase 2 (NOS2) suggesting its role in regulating HIF-1α signalling pathway. The p-methoxyphenyl-substituted derivative 10g displayed specific anti-cytomegalovirus (CMV) potential, whereas aliphatic-substituted derivatives 8l and 8m had the most potent, yet relatively non-specific, anti-varicella-zoster (VZV) activity.

Synthesis, structural studies, and cytostatic evaluation of 5,6-di-O-modified L-ascorbic acid derivatives

The 5,6-di-O-tosylated derivative of L-ascorbic acid was synthesized by selective protection and deprotection of 2,3- and 5,6-dihydroxy functional groups involving 5,6-ditosylation in the final step, while the novel 6-acetoxy, 6-hydroxy, and 6-chloro deri

Continuous flow-ultrasonic synergy in click reactions for the synthesis of novel 1,2,3-triazolyl appended 4,5-unsaturated l-ascorbic acid derivatives

A combination of flow chemistry and batch-based synthetic procedures has been successfully applied to the assembly of novel 4,5-unsaturated l-ascorbic acid series 6a-6n with diverse C-6-substituted 1,2,3-triazole moiety. We report herein the first Cu(i)-catalyzed 1,3-dipolar cycloaddition of azido functionalized l-ascorbic acid derivative and selected alkynes to provide target 1,2,3-triazolyl appended 4,5-didehydro-5,6-dideoxy-l-ascorbic acid library 6a-6n under both micro-flow and batch conditions. Implementation of ultrasound with flow chemistry accelerated hour-scale reaction conditions in batch to the minute range in micro-flow device and considerably improved the yields for the flow syntheses of 6a-6n. Moreover, the synergistic use of microreactor technology and ultrasonic irradiation highlights the sustainable eco-friendly aspect of utilized method.