58769-33-8

Usage

Chemical Category

Carbohydrates

Type

Derivative of ribofuranose

Ribofuranose

A form of sugar

Derivative

Methylated and acetylated

Benzoyl group

Attached to the 5th carbon

Acetyl groups

On the 1st and 2nd carbons

Common use

Organic synthesis

Building block

Creation of various compounds

Structure and properties

Useful in pharmaceuticals and agrochemicals development

Upstream product

• 10300-20-6 5-O-benzoyl-1,2-O-isopropylidene-3-O-methyl-α-D-ribofuranose 
• 108-24-7 acetic anhydride 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 6612-91-5 ((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 
• 64-19-7 acetic acid 

Relevant academic research and scientific papers

Cyclic dinucleotide analogues, pharmaceutical composition of analogues and applications of analogues and pharmaceutical composition

The invention discloses cyclic dinucleotide analogues, a pharmaceutical composition of the analogues and applications of the analogues and the pharmaceutical composition. The cyclic dinucleotide analogs (I), an isomer, prodrug, stable isotope derivative or pharmaceutically acceptable salt of the analogs have a structure shown in the specification. The cyclic dinucleotide analogs provided by the invention can be used as regulators of stimulator of interferon genes (STIG) and related signaling pathways, and can effectively treat and/or alleviate multiple types of diseases, including but not limited to malignant tumors, inflammation, autoimmune diseases and infectious diseases; and in addition, the STING regulators can also be used as vaccine adjuvants.

Total synthesis of mycalisine B

The first total synthesis of the marine nucleoside Mycalisine B-a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside-has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-O-acetyl-ribose and tetracyanoethylene. Key steps of the approach include: (1) I2 catalyzed acetonide formation from 1,2,3,5-tetra-O-acetylribose and acetone at large scale; (2) Vorbrüggen glycosylation using N4-benzoyl-5-cyano-6-bromo-7H-pyrrolo[2,3-d]pyrimidine as a nucleobase to avoid formation of N-3 isomer; (3) mild and scalable reaction conditions.

A total synthesis of mycalisine A

In this paper, we report a total synthesis of a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside, mycalisine A. Our synthetic strategy uses d-xylose as the starting material and Vorbrüggen glycosylation as the key step. Mycalisine A was synthesized in 11 steps with a 15% overall yield.