Convenient Access to 2‐β‐d‐Glucopyranosylpyridines by Using Bohlmann–Rahtz Heteroannulation

Abstract

Convenient synthesis of 2‐β‐d‐Glucopyranosylpyridines has been achieved by using Bohlmann–Rahtz heteroannulation reaction between a sugar alkynone and ethyl β‐aminocrotonate. The synthesized compounds are analogues of Dapagaliflozin, an approved drug for lowering of blood glucose levels through inhibition of sodium‐glucose transporters in the kidney.

Acyl and Benzyl‐C‐β‐D‐Glucosides: Synthesis and Biostudies for Glucose‐Uptake‐Promoting Activity in C2C12 Mytotubes

“…Multigram quantities of building block 6a, 1-formyl--C-glucoside were prepared according to the method described by Frederic Labeguere. [17] The addition of simple alkynylmagnesium bromide and phenylmagnesium bromide at 0°C, led to the formation of corresponding addition products 7a [9] and 7b [16] along with recovery of starting material 6a (10-15 %)(entry 1 and 2 in Table 1). However, in an attempt to optimize and generalize the addition of few other Grignard reagents, extensive formation of elimination product 8 was also observed.…”

“…Theoretically four disconnections are possible for the synthesis of acyl- . [9] No synthetic route is available based on disconnection III, through utilization of synthon C. Disconnection IV envisaging use of synthon D seems to be the most attractive, as it demands mere addition of ArMgX onto C- 1-functionalized D-glucose building blocks such as 6a or 6b. The synthetic route based on disconnection I demands stringent reaction conditions for the formation of C1-carbanionic organometallic equivalent for the synthon A.…”

The Emerging Promise with O/C‐Glycosides of Important Dietary Phenolic Compounds

“…With these substrates, two-step reaction sequence involving radical mediated deoxygenation method and Lewis's acid mediated debenzylation afforded the corresponding targeted compounds 156 f-i. [175] The synthesis of isocoumarin based C-glucoside 157 in particular and 3-glycosylated isocoumarins 174 in general, was based on the use of Julia olefination reaction for CÀ C bond formation between glycosyl-aldehydes 175 and sulfone building blocks 176/177. The carbanion derived from sulfone building blocks 176 [176] and 177 [177] reacted with various monosaccharide derived glycosyl aldehydes 175 a-c (few representatives) and the corresponding products 178 a-c and 179 a-c respectively were obtained in good yields (60-86 %).…”

Natural Products & Bioactivity Inspired Synthetic Pursuits Interfacing with Carbohydrates: Ongoing Journey with C‐Glycosides

“…With substrate 119 f , dechlorinated product 103 f was obtained, while with substrates 119 g‐i , surprisingly, no reaction was observed under hydrogenation conditions. With these substrates, two‐step reaction sequence involving radical mediated deoxygenation method and Lewis acid mediated debenzylation afforded the corresponding targeted compounds 103 f – i [92] …”

“…With these substrates, two-step reaction sequence involving radical mediated deoxygenation method and Lewis acid mediated debenzylation afforded the corresponding targeted compounds 103 f-i. [92] For the synthesis of isocoumarin based C-glucoside 104 in particular and 3-glycosylated isocoumarins 121 in general, the retrosynthetic Scheme as depicted in Figure 15 was visualized.…”