19139-73-2

Upstream product

• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 100-44-7 benzyl chloride 
• 3673-14-1 2,3:4,5-di-D-isopropylidene-D-xylose diethyl dithioacetal 
• 30737-85-0 2,3,4,5-di-O-isopropylidene-D-xylitol 
• 100-39-0 benzyl bromide 
• 13039-94-6 2,3,4,5-di-O-isopropylidene-D-xylose aldehyde 
• 38145-93-6 1,2:3,4-di-O-isopropylidene-D-mannitol 
• 3969-59-3 mannitol triacetonide 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 

Downstream Products

• 346588-20-3 1-O-benzyl-2,3-O-(1-methylethylidene)-D-arabinitol 
• 81801-09-4 4-O-benzyl-2,3-O-isopropylidene-D-threose 
• 66018-41-5 zeaenol 
• 143360-25-2 (S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol 

Relevant academic research and scientific papers

Towards stereoselective synthesis of the C(31)-C(39) and C(20)-C(27) fragments of phorboxazole A

The stereoselective synthesis of the C(31)-C(39) and C(20)-C(27) fragments of phorboxazole A (1) was achieved from commercially available and inexpensive D-mannitol. Crimmins aldol reaction and a decarboxylative Claisen-type reaction are the key steps for

Convergent and stereoselective synthesis of (-)-zeaenol

Stereoselective synthesis of (-)-zeaenol has been accomplished from d-xylose as a chiral pool starting material. The key steps of this convergent synthetic strategy involves a Stille coupling, a Noyori reduction, a Julia-Kocienski olefination and a macrolactonization to obtain (-)-zeaenol. We have also explored a Sonogashira coupling along with a Trost protocol for the intramolecular hydrosilylation on the homopropargylic alcohol system as an alternative synthetic approach to this molecule.

A new approach to (+)-anisomycin

An efficient approach to enantiomerically pure (+)-deacetylanisomycin 2a and a formal synthesis of (+)-anisomycin 2 (11% overall yield in 10 steps) have been achieved through simple and good yielding reactions, starting from 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol 3. Grignard reaction and intramolecular cyclisation reactions are key steps in the strategy.

Synthesis and biological evaluation of new cross-conjugated dienone marine prostanoid analogues

The synthesis of a series of brominated cross-conjugated dienones, marine prostanoid analogues, was considered using two cyclopentannelation processes, from enamine (by a domino 3-aza Claisen/Mannich reaction) and from dioxolane ester alkylation followed by intramolecular Wittig reaction. All the compounds synthesized featured the same cross-conjugated dienone system, with a vicinal syn or anti diol on the ω-chain. The replacement of the ω-side-chain of the natural prostanoids with a 1-hydroxyphenyl-butyl moiety gave new prostanoids (32-34) with good cytotoxicities. In a second series of products, the possibility of a shorter α-side-chain bearing a simple phenyl ester was investigated. The results indicated a dramatic increase in the cytotoxicity (39, 40, 43, 44). Finally, in a third series, the ω- 1-hydroxyphenyl-butyl was replaced by a 1-hydroxymethyloxybenzyl chain. These simpler compounds (45,46,47,48, 60) are still highly cytotoxic, in the medium range of 60 nM, close to the value of natural punaglandins.