87604-53-3

Basic information

• Product Name: (R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane
• Synonyms: (R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane
• CAS NO: 87604-53-3
• Molecular Weight: 262.349
• Mol File: 87604-53-3.mol

Chemical Properties

• CAS DataBase Reference: (R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane(87604-53-3)
• EPA Substance Registry System: (R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane(87604-53-3)

Safety Data

• Hazardous Substances Data: 87604-53-3(Hazardous Substances Data)

Upstream product

• 79364-35-5 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 100-39-0 benzyl bromide 
• 87604-46-4 (2R,3R)-1,2-O-isopropylidene-5-hexene-1,2,3-triol 
• 100-44-7 benzyl chloride 
• 99493-25-1 diisopropyl (R,R)-2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 400710-04-5 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 

Downstream Products

• 699000-02-7 ((2R,3R,5S)-3-Benzyloxy-5-iodomethyl-tetrahydro-furan-2-yl)-methanol 
• 1431373-88-4 (S)-benzyl-(2-benzyloxy-pent-4-enyl)carbamic acid benzyl ester 
• 1431373-89-5 (S)-4-(benzyl-benzyloxycarbonyl-amino)-3-benzyloxy-butyric acid 
• 216063-62-6 (S)-1-benzyl-4-benzyloxy-pyrrolidin-2-one 
• 1431373-84-0 ?(S)-2-(2-benzyloxy-pent-4-enylamino)acetamide 
• 1431373-85-1 (S)-(2-benzyloxy-pent-4-enyl)carbamoylmethyl-carbamic acid benzyl ester 
• 1431373-86-2 (S)-3-benzyloxy-4-(benzyloxycarbonyl-carbamoylmethyl-amino)butyric acid 
• 1431373-87-3 (S)-benzyl-(2-benzyloxy-pent-4-enyl)amine 
• 1337989-74-8 (((2R,3S)-1,3-bis(benzyloxy)-4-(oxiran-2-yl)butan-2-yl)oxy)(tert-butyl)dimethylsilane 
• 1337989-71-5 1-((4S,5R)-4,6-bis(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexyl)-5-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-pyrrole-2-carbaldehyde 

Relevant articles and documents

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).

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Stereoselective iodine-induced cyclisation of alkene acetals. Application to the synthesis of 3-deoxy-exo-glycals and substituted tetrahydrofurans

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