97514-85-7

Basic information

• Product Name: (2E)-4,7-anhydro-2,3,8-trideoxy-2,4-dimethyl-6-C-methyl-D-gulo-oct-2-enose
• CAS NO: 97514-85-7
• Molecular Formula: C₁₁H₁₈O₄
• Molecular Weight: 214.2582
• Mol File: 97514-85-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 324.9°C at 760 mmHg
• Flash Point: 120.5°C
• Density: 1.189g/cm³
• Vapor Pressure: 1.85E-05mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: (2E)-4,7-anhydro-2,3,8-trideoxy-2,4-dimethyl-6-C-methyl-D-gulo-oct-2-enose(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-4,7-anhydro-2,3,8-trideoxy-2,4-dimethyl-6-C-methyl-D-gulo-oct-2-enose(97514-85-7)
• EPA Substance Registry System: (2E)-4,7-anhydro-2,3,8-trideoxy-2,4-dimethyl-6-C-methyl-D-gulo-oct-2-enose(97514-85-7)

Safety Data

• Hazardous Substances Data: 97514-85-7(Hazardous Substances Data)

Upstream product

• 102103-89-9 (E)-3-(3α,4α-dihydroxy-2β,4β,5β-trimethyltetrahydrofuran-2α-yl)-2-methylprop-2-en-1-ol 
• 102103-83-3 (2E,4RS,5RS)-4,5-isopropylidenedioxy-2,4-dimethylhex-2-enal 
• 102103-85-5 (2E,4E,6RS,7RS)-ethyl 6,7-dihydroxy-2,4,6-trimethylocta-2,4-dienoate 
• 102103-84-4 (2E,4E,6RS,7RS)-ethyl 6,7-isopropylidenedioxy-2,4,6-trimethylocta-2,4-dienoate 
• 102103-82-2 (2E,4RS,5RS)-ethyl 4,5-isopropylidenedioxy-2,4-dimethylhex-2-enoate 
• 104417-90-5 (2E,4RS,5RS)-4,5-isopropylidenedioxy-2,4-dimethylhex-2-en-1-ol 
• 102103-86-6 (E)-3-[3-(1,2-Dihydroxy-1-methyl-propyl)-2-methyl-oxiranyl]-2-methyl-acrylic acid ethyl ester 
• 102103-86-6 (E)-3-[(2S,3S)-3-((1R,2S)-1,2-Dihydroxy-1-methyl-propyl)-2-methyl-oxiranyl]-2-methyl-acrylic acid ethyl ester 
• 110510-61-7 (+/-)-(2S^*,3S^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-4-ol 
• 98095-65-9 (+/-)-(2R^*,3S^*,4S^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2-(1-iodoethyl)-2,4,5-trimethyl-3-tetrahydrofuranyl benzoate 
• 98095-63-7 (+/-)-(2R^*,3S^*,4S^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2-(1-iodoethyl)-2,4,5-trimethyl-3-tetrahydrofuranol 
• 107613-13-8 Benzoic acid (Z)-(R)-1-[(1R,2S)-2-benzyloxy-1-(2-methoxy-ethoxymethoxy)-1-methyl-propyl]-2-methyl-but-2-enyl ester 
• 98168-77-5 (+/-)-(2S^*,3S^*,4S^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranyl benzoate 
• 110510-59-3 (+/-)-(2S^*,3S^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran 

Relevant articles and documents

Total synthesis of (±)-citreoviral

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New Stereoselective Approach to Hydroxy-Substituted Tetrahydrofurans. Total Synthesis of (+/-)-Citreoviral

A concise total synthesis of (+/-)-citreoviral which illustrates a new stereoselective approach to hydroxy-substituted tetrahydrofurans is described.Key features in the synthesis are: (i) elaboration of the Z-unsaturated epoxy ester 10, (ii) acid-catalysed cyclisation of ester 10 to the 4-hydroxyethyl-substituted but-2-enolide 14, (iii) stereoselective vicinal hydroxylation of the butenolide 14 to the diol 15, (iv) cyclic ether formation from diol 15 to the bicyclic lactone 8 via the benzylidene acetal 9, (v) transesterification of bicycle 8 to the tetrahydrofuran 21 containing three of the four centres in citreoviral in the correct relative configuration.Inversion of the secondary 3-OH group in compound 21, and elaboration of the C-2 side-chain, then completed the synthesis of (+/-)-citreoviral.

Total Synthesis of (+/-)-Citreoviridin

Investigations of iodine-induced cyclizations of γ,δ-olefinic benzyl ethers have led to highly substituted tetrahydrofurans from acyclic precursors with excellent stereochemical control.Our studies have afforded total syntheses of two fungal metabolites,