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Synthesis of protected glucose derivatives from levoglucosan by development of common carbohydrate protecting group reactions under continuous flow conditions
- Source :
- Carbohydrate Research. 468:23-29
- Publication Year :
- 2018
- Publisher :
- Elsevier BV, 2018.
-
Abstract
- Common carbohydrate protecting group reactions under continuous flow processes are reported in the context of producing partially-protected glucose building blocks from levoglucosan. Benzyl ether protection was demonstrated without the use of NaH using barium oxide, which, however, pointed to the need for forms of this catalyst not as susceptible to close packing under flow. Acylation conditions were developed under continuous flow in acetonitrile and avoiding pyridine. Ring-opening the derivatized levoglucosan with propanethiol was also demonstrated producing S-alkyl 2,4-di-O-benzyl-glucopyranoside building block in 2 rather than 12 steps in increased overall yield.
- Subjects :
- 010405 organic chemistry
Acylation
Levoglucosan
Organic Chemistry
Propanethiol
Context (language use)
Chemistry Techniques, Synthetic
General Medicine
Carbohydrate
010402 general chemistry
01 natural sciences
Biochemistry
Article
0104 chemical sciences
Analytical Chemistry
Catalysis
chemistry.chemical_compound
Glucose
chemistry
Pyridine
Organic chemistry
Protecting group
Subjects
Details
- ISSN :
- 00086215
- Volume :
- 468
- Database :
- OpenAIRE
- Journal :
- Carbohydrate Research
- Accession number :
- edsair.doi.dedup.....633bf8eaf120230e1ef8d2efd19fd6a3