137501-12-3

Basic information

• Product Name: (3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol
• CAS NO: 137501-12-3
• Molecular Weight: 265.104
• Mol File: 137501-12-3.mol
• Article Data: 26

Chemical Properties

• CAS DataBase Reference: (3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol(137501-12-3)
• EPA Substance Registry System: (3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol(137501-12-3)

Safety Data

• Hazardous Substances Data: 137501-12-3(Hazardous Substances Data)

Upstream product

• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 
• 108-86-1 bromobenzene 
• 130669-74-8 (1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol 
• 130669-75-9 (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 77-76-9 2,2-dimethoxy-propane 
• 82683-92-9 1-Bromo-2,3-dihydroxy-cyclohexa-4,6-diene 

Downstream Products

• 154013-20-4 (1R,2R,3S,4S)-5-bromo-5-cyclohexene-1,2,3,4-tetraol 
• 900791-79-9 (1S,2R,5S,6S)-6-(acetyloxy)-2,3,5-tribromo-3-cyclohexenyl acetate 
• 1393364-60-7 (1R,2R,3R,4R)-1,2-O-diacetyl-5-phenylcarbamoyl-3,4-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetraol 
• 1393364-63-0 (1S,2R,3R,4R)-1,2-O-diacetyl-5-phenylcarbamoyl-3,4-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetraol 
• 130698-44-1 (3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol 
• 1572455-10-7 C₁₆H₁₉BrO₅ 

Relevant articles and documents

Efficient and enantiodivergent synthesis of (+)- and (-)-pinitol

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Chemoenzymatic Synthesis of the Antifungal Compound (–)-Pestynol by a Convergent, Sonogashira Construction of the Central Yne-Diene

A total synthesis of the fungal-derived natural product pestynol is reported via a convergent chemoenzymatic approach from the readily available precursors geranyl bromide, ethyl acetoacetate, trimethylsilylacetylene, and bromobenzene. Synthetic (–)-pestynol proved to be identical in all respects to the natural material, allowing confirmation of the structure including absolute stereochemistry.

Synthesis of a Highly Functionalised and Homochiral 2-Iodocyclohexenone Related to the C-Ring of the Polycyclic, Indole Alkaloids Aspidophytine and Haplophytine

The enzymatically-derived and enantiomerically pure (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (7) has been elaborated over 10 steps into cyclohexenone 8. The latter compound embodies the enantiomeric form of the C-ring associated with the hexacyclic framework of the alkaloid aspidophytine (2). As such, this work sets the stage for effecting the conversion of the enantiomeric metabolite ent-7 into compound ent-8, and thence, through previously established protocols, including a palladium-catalysed Ullmann cross-coupling reaction, into the title alkaloids.