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

• 130669-76-0 (3aS,4R,5R,7aR)-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole-4,5-diol 
• 596834-79-6 (3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene 
• 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 

Relevant articles and documents

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

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Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer

This manuscript describes the enantioselective synthesis of the aminocyclitol moiety of the antibiotic hygromycin A in eight steps and 39 % overall yield from a non-chiral starting material. The sequence made use of an initial enzymatic step to transfer chirality to an aromatic ring and was followed by selective organic chemistry transformations (oxidation, pro-tection, azidation, hydrolysis) of the six-membered ring in order to achieve the target. The approach is also amenable to the synthesis of other related unnatural analogues as exemplified by the synthesis of the C2 epimer of the natural aminocyclitol. All the intermediates were fully characterized, and the absolute stereochemistry assigned by spectrometric methods.

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.