99838-68-3

Upstream product

• 942137-19-1 (2R)-2-[(1S)-1-(benzyloxy)-3-butenyl]-1,4-dioxaspiro[4.5]decane 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 400710-04-5 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 164145-69-1 1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol 
• 79364-35-5 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 87604-53-3 (2R)-3-benzyloxy-1,2-di-O-isopropylidene-5-hexen-1,2-diol 
• 87604-54-4 (R)-4-((R)-1-(benzyloxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane 
• 87604-53-3 (R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane 

Downstream Products

• 942137-20-4 (R)-2-[(S)-1-(benzyloxy)but-3-enyl]oxirane 
• 99838-70-7 (2R,3S)-3-benzyloxy-1-tosyloxy-5-hexen-2-ol 
• 99838-71-8 (2R,3R)-3-benzyloxy-1-tosyloxy-5-hexen-2-ol 
• 1254513-45-5 ((2R,3S)-3-(benzyloxy)-2-[(4-methoxybenzyl)oxy]-5-hexenyloxy)(tert-butyl)dimethylsilane 

Relevant academic research and scientific papers

Attempts towards the synthesis of mupirocin-H

The stereoselective synthesis of segments C1-C6 (3), C7-C12 (4) of mupirocin-H has been achieved. The synthetic procedure for the C1-C6 segment includes the zinc mediated allyl Grignard reaction with Rglyceraldehyde, Swern oxidation/Witting olefination reactions and followed by Sharpless asymmetric epoxidation. The C7-C12 segment was synthesized using again Sharpless asymmetric epoxidation on mono PMB protected 2-butene-1,4-diol, followed by regioselective opening of this epoxide with trimethyl aluminium. Both segments C1-C6 (3) and C7-C12 (4) possesses the five new stereogenic centers along with trans-olefin, but in various attempts condensation of 3 and 4 segments to give C-C bond forming parent segment (2) not affirmed, hence this work constitutes the synthesis of fragments C1-C6 (3) and C7-C12 (4) of mupirocin-H. {figure presented}

An Enantioselective Synthesis of (5 S,6 R,11 S,14 R)-Acremodiol

An expeditious synthesis of the (5 S,6 R,11 S,14 R)-isomer of acremodiol was developed via a convergent route. One of the required building blocks was synthesized earlier via two sequential lipase-catalyzed secondary carbinol acetylations. The other unit

Selective synthetic method of natural products Xylapyrroside A

The invention belongs to the field of chemical synthesis, and relates to a selective synthetic method of natural products Xylapyrroside A. According to the invention, (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-formaldehyde is taken as an initial raw material, a Grignard reaction, hydroxy benzyl protection, acetonide protection removal, hydroxy selective tert-butyl dimethyl silicon and benzyl protection, terminal double bond epoxidation and iodo ring opening and oxidation are carried out to obtain (4S,5R)-4,5-di-benzyloxy-6-tert-butyldimethylsilyloxy-1-n-amyl iodide-2-ketone, the product is subjected to condensation with another intermediate 5-(((tetrahydro-2H-pyrans-2-group)oxygen)methyl)-1H-pyrroles-2-formaldehyde under alkaline condition, and then the product is subjected to deprotection and cyclization, and finally the target product is synthesized. The method has the advantages of simple operation and high yield, and a reagent has the advantages of low cost and easy acquisition of the raw materials.

Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: Isolation, complete structure elucidation, and total syntheses

Two new [named xylapyrrosides A (1) and B (2)] along with two known [pollenopyrrosides A (3) and B (=acortatarin A, 4)] naturally occurring spirocyclic pyrrole alkaloids were isolated and identified as minor components from the EtOH extract of the dried mycelia of the edible medicinal fungus Xylaria nigripes. Their structures were established by a combination of interpretation of spectroscopic data and single-crystal X-ray diffraction analyses. The isolates possess a unique tricyclic skeleton comprising a common bicyclic 2-formyl-pyrrole-fused morpholine, with a variable ketohexoside ring. This class of alkaloids is quite rare from natural sources. In this study, the total syntheses of compounds 1, 2 and 4 were successfully achieved by two alternative strategies, and three new analogs [named xylapyrrosides A1 (1a), A2 (1b) and B1 (2a)] were also produced. Notably, the total synthesis of such spiroketal alkaloids with a pyranose ring (e.g.,1) was accomplished for the first time. The absolute configurations of the new isolates can be thereafter unequivocally secured by the total syntheses. The above isolated and synthesized spiro-alkaloids were found to show moderate antioxidant effects by preventing the oxidative stress-induced cytotoxicity of A7r5 rat vascular smooth muscle cells (VSMCs).

The protecting-group directed diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction: Total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues

The stereoselective total synthesis of zeaenol and 7-epi-zeaenol is achieved in a convergent manner using Julia-Kocienski olefination, protecting group-directed intermolecular diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction, De Brabander's lactoniza

Synthesis of the unusual α-amino acid component of some novel histone deacetylase inhibiting cyclic peptides

A flexible protocol for the synthesis of three lipophilic α-amino acid components of some novel cyclic peptides having important histone deacetylase inhibiting properties has been developed from a common source, which featured a cross-metathesis reaction

Stereoselective total synthesis of verbalactone

A simple and efficient route for the stereoselective total synthesis of verbalactone from commercially available inexpensive starting material d-mannitol using Barbier allylation, α-aminoxylation, and Yamaguchi macrolactonization as key steps is reported.

Stereoselective synthesis of (S)-oxiracetam and (S)-GABOB from (R)-glyceraldehyde acetonide

Synthetic routes to (S)-oxiracetam and (S)-GABOB have been developed starting from (R)-glyceraldehyde acetonide through its conversion to an appropriate aldehyde intermediate followed by reductive amination using glycinamide hydrochloride/benzyl amine and subsequent chemical transformations.

First Total Synthesis of (3 R,4 S)-4-Hydroxylasiodiplodin: A Facile and Stereoselective Approach

A first total synthesis of (3R,4S)-4-hydroxylasiodiplodin is described starting from methyl acetoacetate and a commonly available carbohydrate, d-mannitol, which is regularly used in organic synthesis. The facile and stereoselective approach involves the

Stereoselective total synthesis of cytotoxic sporiolide A

A simple and highly efficient stereoselective total synthesis of cytotoxic agent sporiolide A has been achieved starting from d-mannitol; the strategy of synthesis utilizes stereoselective zinc-mediated allylation, aldol coupling and ring-closing metathes