317821-92-4

Basic information

• Product Name: 5,6-DIBROMO-2-CYCLOHEXENE-1,4-DIOL
• Synonyms: 5,6-DIBROMO-2-CYCLOHEXENE-1,4-DIOL
• CAS NO: 317821-92-4
• Molecular Formula: C₆H₈Br₂O₂
• Molecular Weight: 271.93
• Mol File: 317821-92-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,6-DIBROMO-2-CYCLOHEXENE-1,4-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIBROMO-2-CYCLOHEXENE-1,4-DIOL(317821-92-4)
• EPA Substance Registry System: 5,6-DIBROMO-2-CYCLOHEXENE-1,4-DIOL(317821-92-4)

Safety Data

• Hazardous Substances Data: 317821-92-4(Hazardous Substances Data)

Upstream product

• 106-51-4 p-benzoquinone 

Downstream Products

• 639079-40-6 (1R,2S,3R,6S)-6-azido-2-bromocyclohex-4-ene-1,3-diol 
• 251538-17-7 (1S,2R,3S,6R)-6-azido-2-bromocyclohex-4-ene-1,3-diol 
• 170210-89-6 (+)-(1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene 
• 93752-54-6 LL-C10037α 
• 169529-92-4 (+)-(1R,2S,3S,4R)-2,3-dibromocyclohex-5-ene-1,4-diol 
• 112212-81-4 (+/-)-(1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene 

Relevant articles and documents

New Stereoselective Route to the Epoxyquinol Core of Manumycin-Type Natural Products. Synthesis of Enantiopure (+)-Bromoxone, (-)-LL-C10037α, and (+)-KT 8110

A practical route is decribed for the preparation of the C7N core of manumycin-type compounds. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol. A diepoxy aminoinositol is accessible which can function for formation of enantiopure epoxyquinones and quinols. Examples are given for acylation reactions of this amine with several acyl derivatives. With this approach (-)-LL-C10037α and quinones such as (+)-KT-8110 with 5A,6S-configuration can be synthesized through oxidation. In addition a short route to (+)-bromoxone is described. Most steps include simple epoxide formation and cleavage reactions which all can be carried out in a high stereoselective manner.