27267-71-6

Basic information

• Product Name: gamma-rubromycin
• Synonyms: gamma-rubromycin;(S)-4,5',8',9-Tetrahydro-4',9',10-trihydroxy-7'-methoxy-5',8',9-trioxospiro[benzo[1,2-b:5,4-c']dipyran-2(3H),2'(3'H)-naphtho[2,3-b]furan]-7-carboxylic acid methyl ester;(2S)-4,5',8',9-Tetrahydro-4',9',10-trihydroxy-7'-methoxy-5',8',9-trioxospiro[benzo[1,2-b:5,4-c']dipyran-2(3H),2'(3'H)-naphtho[2,3-b]furan]-7-carboxylic acid methyl ester
• CAS NO: 27267-71-6
• Molecular Formula: C26H18O12
• Molecular Weight: 522.41392
• Mol File: 27267-71-6.mol

Chemical Properties

• Boiling Point: 909.3°Cat760mmHg
• Flash Point: 313.4°C
• Appearance: /
• Density: 1.77g/cm³
• PKA: 6.30±0.40(Predicted)
• CAS DataBase Reference: gamma-rubromycin(CAS DataBase Reference)
• NIST Chemistry Reference: gamma-rubromycin(27267-71-6)
• EPA Substance Registry System: gamma-rubromycin(27267-71-6)

Safety Data

• Hazardous Substances Data: 27267-71-6(Hazardous Substances Data)

Usage

Uses

gamma-Rubromycin (cas# 27267-71-6) is a compound useful in organic synthesis.

Upstream product

• 151158-33-7 4-Chloro-purpuromycin 
• 53969-01-0 purpuromycin 
• 151158-08-6 4-O-(Tetrahydro-2H-pyran-2-yl)-purpuromycin 
• 182174-42-1 4',9',10-Tris-O-acetyl-4-O-(methylsulfonyl)-purpuromycin 
• 151158-09-7 4',9',10-Triacetyl-4-O-(tetrahydro-2H-pyran-2-yl)-purpuromycin 
• 959587-11-2 C₂₉H₂₄O₁₂ 
• 1198596-64-3 C₁₃H₁₁N₃O₅ 
• 13261-43-3 2-hydroxy-5,7,8-trimethoxy-1,4-naphthoquinone 
• 1286186-29-5 C₁₆H₁₄O₆ 
• 1286186-42-2 C₂₉H₂₄O₁₂ 
• 1286186-44-4 C₂₉H₂₄O₁₂ 
• 2644-68-0 2,5,7,8-tetramethoxy-1,4-naphthoquinone 
• 2020-88-4 5,7,8-trimethoxy-α-tetralone 
• 136008-98-5 2-bromo-5,7,8-trimethoxynaphthalen-1-ol 

Relevant articles and documents

A convergent total synthesis of the telomerase inhibitor (±)-γ-rubromycin

The total synthesis of the human telomerase inhibitor γ-rubromycin in its racemic form was accomplished in 3.8 % overall yield. The key feature of this synthesis is an efficient acid-catalyzed spiroketalization for the construction of the spiroketal core. The required electronically well-balanced spiroketal precursor was obtained by the convergent assembly of a naphthyl-substituted aldehyde, an α-methoxyallyl-γ-silyl-substituted phosphonate as the central C3 building block, and a highly functionalized aryl Grignard reagent. Another key feature is the late-stage construction of the isocoumarin moiety and a simultaneous protodesilylation furnishing the known methyl aryl ether protected precursor of γ-rubromycin. 3 building blocks + 3 acids→natural product: After the assembly of the crucial precursor from three highly functionalized building blocks, the pivotal spiroketalization was achieved with trifluoromethanesulfonic acid, the isocoumarin formation with fluoroboric acid, and the O-demethylation with the Lewis acid boron tribromide. (±)-γ-Rubromycin was thus synthesized in 18 steps with an overall yield of 3.8 % from commercially available precursors.

A convergent total synthesis of (±)-γ-rubromycin

An expeditious convergent total synthesis affords (±)-γ- rubromycin (1) in 4.4% overall yield. The longest linear sequence is 12 steps from commercial starting materials. The effort highlights a remarkable late-stage oxidative [3 + 2] cycloaddition for co

Total synthesis of (±)-γ-rubromycin on the basis of two aromatic pummerer-type reactions

(Chemical Equation Presented) Double or nothing: In a convergent synthesis of the title compound, a potent inhibitor of human telomerase, two different aromatic Pummerer-type reactions were employed to construct the pivotal bisbenzannelated spiroketal ske

Synthesis and antimicrobial activities of 4-purpuromycin derivatives

Purpuromycin (1) is a natural antibiotic with a broad spectrum of activity encompassing bacteria fungi and protozoa. A new series of derivatives of 1 was prepared by the modification or replacement of the C-4 hydroxyl group. The physico-chemical characteristics and the in vitro antimicrobial activity of these new semisynthetic purpuromycin derivatives are reported. Attachment of a variety of bulky groups to the C-4 hydroxyl group as well as acylation or mesylation of 1 gave derivatives with significantly reduced antifungal activity, while the antimicrobial activity of these derivatives against Gram-positive and Gram-negative bacteria was only slightly decreased. All compounds were inactive against Escherichia coli. The C-4 epimers showed different in vitro activity as compared with those having the natural configuration, particularly against fungi.