56681-97-1

Basic information

• Product Name: 4,4-Dimethoxybutanal
• Synonyms: 4,4-Dimethoxybutanal;4,4-Dimethoxybutyraldehyde
• CAS NO: 56681-97-1
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.15768
• Mol File: 56681-97-1.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4,4-Dimethoxybutanal(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-Dimethoxybutanal(56681-97-1)
• EPA Substance Registry System: 4,4-Dimethoxybutanal(56681-97-1)

Safety Data

• Hazardous Substances Data: 56681-97-1(Hazardous Substances Data)

Upstream product

• 63284-78-6 (4Z)-1,1,8,8-tetramethoxyoct-4-ene 
• 4220-66-0 methyl 4,4-dimethoxybutanoate 
• 6044-68-4 3,3-dimethoxyprop-1-ene 
• 107-02-8 acrolein 
• 14618-78-1 4,4-dimethoxybutanenitrile 
• 67-56-1 methanol 
• 1165952-91-9 cyclohexa-1,3-diene 

Downstream Products

• 332072-71-6 (R)-(-)-N-(4,4-dimethoxybutanylidene)-p-toluenesulfinimide 
• 911857-32-4 4-(3,3-dimethoxypropyl)-6-phenyl-2-pyrazol-1-yl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester 
• 902454-51-7 C₁₈H₂₈O₄ 
• 902454-52-8 C₂₂H₃₄O₆ 
• 902454-53-9 C₂₀H₃₂O₅ 
• 911857-42-6 2-amino-6-(3,3-dimethoxypropyl)-4-phenyl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester 
• 911857-37-9 6-(3,3-dimethoxypropyl)-4-phenyl-2-pyrazol-1-yl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester 
• 911857-43-7 2-amino-6-(3,3-dimethoxypropyl)-4-(4-nitrophenyl)-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester 
• 911857-38-0 6-(3,3-dimethoxypropyl)-4-(4-nitrophenyl)-2-pyrazol-1-yl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester 
• 823785-38-2 4-methoxy-6-phenylhex-5-ynal 
• 135781-97-4 2-benzyl-3-methoxylcyclopent-2-enone 
• 713525-97-4 (S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-4,4-dimethoxybutylphosphonate 
• 424835-12-1 2-methoxy-5-(3-phenylsulfanyl-but-3-enyl)-tetrahydro-furan 
• 219130-10-6 2-((1E,3E)-7,7-Dimethoxy-3-methyl-hepta-1,3-dienyl)-1,3,3-trimethyl-cyclohexene 

Relevant articles and documents

A Convenient Preparation of 4,4-Dimethoxybutanal by Ozonolysis of 1,5-Cyclooctadiene

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Bioinspired Divergent Oxidative Cyclizations of Geissoschizine: Total Synthesis of (–)-17-nor-Excelsinidine, (+)-16-epi-Pleiocarpamine, (+)-16-Hydroxymethyl-Pleiocarpamine and (+)-Taberdivarine H

We report a full account of our efforts towards bioinspired oxidative cyclizations of geissochizine and analogs to mimic the biosynthesis of the mavacuran, akuammilan, and excelsinidine groups of monoterpene indole alkaloids. The construction of the A,B,C,D ring system of geissoschizine was first achieved by merging two known syntheses of this alkaloid. Modified Ma's oxidative conditions (KHMDS/I2) applied directly to geissoschizine induced formation of the N4–C16 bond encountered in the excelsinidines core. Identical conditions applied to C16-dimethylmalonate-containing N4-quaternized substrates ended in the formation of the mavacurans core (N1–C16 bond). With this unified oxidative cyclization strategy: (–)-17-nor-excelsinidine, (+)-16-epi-pleiocarpamine, (+)-16-hydroxymethyl-pleiocarpamine, 16-formyl-pleiocarpamine and (+)-taberdivarine H were synthetized. We also report a shortened total synthesis of 16-epi-pleiocarpamine compared to our preliminary communication from a C16-monoester analog. Alternatively, 17-nor-excelsinidine was synthesized via an intramolecular nucleophilic substitution of a 7-membered ring α-chlorolactam prepared from 16-desformyl-geissoschizine.

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