The Synthesis of Long‐Chain α‐Alkyl‐β‐Hydroxy Esters Using Allylic Halides in a Fráter–Seebach Alkylation

Khan, Ashna A.; Chee, Stephanie H.; Stocker, Bridget L.; Timmer, Mattie S. M.

doi:10.1002/ejoc.201101472

Cited by 12 publications

(21 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Stirring was continued overnight at room temperature. The mixture was then passed through a short silica gel column and eluted with dichloromethane (20 mL Docos-1-en-3-ol (7): 23 A flame-dried nitrogen-flushed 250 mL three-necked round-bottomed flask, fitted with a condensor and an additional funnel was charged with magnesium turnings (0.14 g, 5.76 mmol) and anhyd. diethyl ether (10 mL).…”

Section: -Bromodecan-1-olmentioning

confidence: 99%

See 1 more Smart Citation

Microwave and Ultrasound Assisted First Synthesis of 12-Hydroxyhentriacontane

Kaur

Jindal

et al. 2015

Journal of Chemical Research

View full text Add to dashboard Cite

An aliphatic alcohol 12-hydroxyhentriacontane has been synthesised for the first time. The synthetic route of this naturally occurring alcohol adopts the techniques of microwave and ultrasonic irradiation. The synthetic approach provided enough material to corroborate the structure of the target molecule which had been isolated from leaves of Ziziphus mauritiana and exhibits excellent anti-inflammatory, antibacterial and antimicrobial properties.

show abstract

Section: -Bromodecan-1-olmentioning

confidence: 99%

“…Docos-1-en-3-ol (7): 23 A flame-dried nitrogen-flushed 250 mL three-necked round-bottomed flask, fitted with a condensor and an additional funnel was charged with magnesium turnings (0.14 g, 5.76 mmol) and anhyd. diethyl ether (10 mL).…”

Section: -Bromodecan-1-ol (3)mentioning

confidence: 99%

Microwave and Ultrasound Assisted First Synthesis of 12-Hydroxyhentriacontane

Kaur

Jindal

et al. 2015

Journal of Chemical Research

View full text Add to dashboard Cite

show abstract

“…To this end, diethyl L-malate (8) was prepared by refluxing L-malic acid (10) with concentrated sulfuric acid in ethanol to provide 8 in excellent (95%) yield (Scheme 4). 73,86 Subsequent Fráter-Seebach alkylation with iodide 7 then gave the alkyl--hydroxy diester 13 in yields exceeding those in the literature (61%) 85 and in a 5:1…”

Section: Preparation Of the Intermediate Epoxide (5)mentioning

confidence: 92%

“…4,84 The mycolic acid 8) is available from L-malic acid (10), 86 while allylic iodide 7 is readily prepared from octadecanol (9) in 3 steps. 85…”

Section: Retrosynthetic Analysismentioning

confidence: 99%

See 1 more Smart Citation

The Synthesis of Modified Trehalose Glycolipids: Towards Understanding Mincle and MCL Binding

Bird¹

View full text Add to dashboard Cite

<p>Trehalose glycolipids are a diverse family of long-chain fatty acid diesters isolated from the cell walls of bacteria, in particular Mycobacterium species including M. tuberculosis. These molecules possess an array of biological activities which contribute to the survival and virulence of the organism,however, it is their activity as potent stimulators of innate and early adaptive immunity for which they are of interest. In particular, trehalose glycolipids have an application as adjuvants in vaccines and immunotherapies, for diseases such as tuberculosis (TB) and cancer. Recently, the macrophage-inducible C-type lectin, Mincle, and the macrophage C-type lectin, MCL, were identified as receptors for trehalose glycolipids, however, the exact mechanisms by which these receptors recognise and bind glycolipids is, as yet, unknown.This thesis presents the synthesis of a variety of structurally diverse trehalose glycolipid analogues. As such, three mycolic acids bearing a C22 α-chain and diversified meromycolate branches were prepared from an epoxide intermediate, itself prepared in eight steps from commercially available starting materials. The mycolic acids were then coupled to TMS-trehalose and subsequently deprotected to give the mono-and diester derivatives, 1a-cand 2c, which will be assessed for their immunostimulatory activity through the activation of wild type and Mincle-/-murine macrophages. This work provides a first step towards determining how the structures of trehalose glycolipids influence Mincle and MCL binding and activity, and allow for the development of improved trehalose glycolipids for use in adjuvant therapies.</p>

show abstract

Synthesis and Biological Evaluation of Simplified Ansellone Analogues with Lipophilic Side Chains as HIV Latency‐Reversing Agents

Yanagihara

Nakahara

Abe

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

Structurally simplified analogues of ansellone A, in which the decalin skeleton is replaced with a lipophilic chain, were prepared and their HIV latency-reversing activities biologically evaluated. In particular, two analogues bearing ether and alkenyl side chains, respectively, showed comparable activities to that of ansellone A. Each of the simplified compounds was easily synthesized using Prins cyclisation chemistry.

show abstract

The Synthesis of Long‐Chain α‐Alkyl‐β‐Hydroxy Esters Using Allylic Halides in a Fráter–Seebach Alkylation

Cited by 12 publications

References 52 publications

Microwave and Ultrasound Assisted First Synthesis of 12-Hydroxyhentriacontane

Microwave and Ultrasound Assisted First Synthesis of 12-Hydroxyhentriacontane

The Synthesis of Modified Trehalose Glycolipids: Towards Understanding Mincle and MCL Binding

Synthesis and Biological Evaluation of Simplified Ansellone Analogues with Lipophilic Side Chains as HIV Latency‐Reversing Agents

Contact Info

Product

Resources

About