79663-49-3

Basic information

• Product Name: 6-[(1E,3E,5E)-6-[(1R,2R,3R,5R,7R,8R)-7-ethyl-2,8-dihydroxy-1,8-dimethy l-4,6-dioxabicyclo[3.3.0]oct-3-yl]hexa-1,3,5-trienyl]-4-methoxy-5-meth yl-pyran-2-one
• Synonyms: 6-[(1E,3E,5E)-6-[(1R,2R,3R,5R,7R,8R)-7-ethyl-2,8-dihydroxy-1,8-dimethy l-4,6-dioxabicyclo[3.3.0]oct-3-yl]hexa-1,3,5-trienyl]-4-methoxy-5-meth yl-pyran-2-one;6-[(1E,3E,5E)-6-[(2R,6aβ)-5β-Ethylhexahydro-3α,4β-dihydroxy-3aβ,4α-dimethylfuro[2,3-b]furan-2α-yl]-1,3,5-hexatrienyl]-4-methoxy-5-methyl-2H-pyran-2-one
• CAS NO: 79663-49-3
• Molecular Formula: C23H30O7
• Molecular Weight: 418.53
• Mol File: 79663-49-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 456.23°C (rough estimate)
• Flash Point: 208.5°C
• Appearance: /
• Density: 1.1614 (rough estimate)
• Vapor Pressure: 1.53E-17mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• PKA: 13.49±0.70(Predicted)
• CAS DataBase Reference: 6-[(1E,3E,5E)-6-[(1R,2R,3R,5R,7R,8R)-7-ethyl-2,8-dihydroxy-1,8-dimethy l-4,6-dioxabicyclo[3.3.0]oct-3-yl]hexa-1,3,5-trienyl]-4-methoxy-5-meth yl-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[(1E,3E,5E)-6-[(1R,2R,3R,5R,7R,8R)-7-ethyl-2,8-dihydroxy-1,8-dimethy l-4,6-dioxabicyclo[3.3.0]oct-3-yl]hexa-1,3,5-trienyl]-4-methoxy-5-meth yl-pyran-2-one(79663-49-3)
• EPA Substance Registry System: 6-[(1E,3E,5E)-6-[(1R,2R,3R,5R,7R,8R)-7-ethyl-2,8-dihydroxy-1,8-dimethy l-4,6-dioxabicyclo[3.3.0]oct-3-yl]hexa-1,3,5-trienyl]-4-methoxy-5-meth yl-pyran-2-one(79663-49-3)

Safety Data

• Hazardous Substances Data: 79663-49-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H30O7/c1-6-18-23(4,26)22(3)20(25)16(29-21(22)30-18)12-10-8-7-9-11-15-14(2)17(27-5)13-19(24)28-15/h7-13,16,18,20-21,25-26H,6H2,1-5H3/b8-7+,11-9+,12-10+/t16-,18-,20+,21+,22+,23+/m1/s1

Upstream product

• 90623-39-5 (1R,3R,4R,5R,6R,7R)-3-ethyl-4,6-dihydroxy-7-<(1E,3E,5RS)-5-hydroxy-6-(4-methoxy-5-methyl-2-pyron-6-yl)hexa-1,3-dienyl>-4,5-dimethyl-2,8-dioxabicyclo<3.3.0>octane 
• 536737-87-8 (E)-3-((2R,3R,3aR,4R,5R,6aS)-5-Ethyl-3,4-dihydroxy-3a,4-dimethyl-hexahydro-furo[2,3-b]furan-2-yl)-propenal 
• 536737-95-8 astelotoxin bis(trimethylsilyl) ether 
• 164365-02-0 (1S,3R,4R,5R,6R,7R)-5,6-dimethyl-7-ethyl-3-(hydroxymethyl)-4-(4-methoxybenzyloxy)-2,8-dioxabicyclo[3.3.0]octan-6-ol 
• 536737-79-8 (2S,3R,3aR,4R,5R,6aR)-5-Ethyl-4-hydroxy-3-(4-methoxy-benzyloxy)-3a,4-dimethyl-hexahydro-furo[2,3-b]furan-2-carbaldehyde 
• 164365-01-9 (1S,3R,4R,5R,6R,7R)-5,6-dimethyl-7-ethyl-4-(4-methoxybenzyloxy)-3-(triisopropylsiloxymethyl)-2,8-dioxabicyclo[3.3.0]octan-6-ol 
• 536737-63-0 (2RS,3R,4R,5R)-3-[(2R,3R)-2,3-dihydroxy-2-pentyl]-5-(triisopropylsiloxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyloxolane 
• 536737-86-7 (2R,3R,3aR,4R,5R,6aS)-2-Ethyl-5-((E)-3-hydroxy-propenyl)-3,3a-dimethyl-hexahydro-furo[2,3-b]furan-3,4-diol 
• 536737-89-0 (1S,3R,4R,5R,6R,7R)-3-(3-acetoxyprop-1(E)-enyl)-4,6-dihydroxy-5,6-dimethyl-7-ethyl-2,8-dioxabicyclo[3.3.0]octane 
• 536737-72-1 (2S,3S,4S,5R)-5-(hydroxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-[2(E)-penten-2-yl]oxolane 
• 536737-93-6 (E)-3-((2R,3R,3aR,4R,5R,6aS)-5-Ethyl-3a,4-dimethyl-3,4-bis-trimethylsilanyloxy-hexahydro-furo[2,3-b]furan-2-yl)-propenal 
• 536737-77-6 (2R,3R,4S)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-5(E)-en-1,2-diol 
• 536737-84-5 (1S,3R,4R,5R,6R,7R)-5,6-dimethyl-7-ethyl-3-(3-hydroxyprop-1(E)-enyl)-4-(4-methoxybenzyloxy)-2,8-dioxabicyclo[3.3.0]octan-6-ol 
• 536738-16-6 (E)-3-((2R,3R,3aR,4R,5R,6aS)-5-Ethyl-3a,4-dimethyl-3,4-bis-trimethylsilanyloxy-hexahydro-furo[2,3-b]furan-2-yl)-prop-2-en-1-ol 

Relevant articles and documents

Total synthesis of (+)-asteltoxin

A convergent synthesis of (+)-asteltoxin (1) has been achieved by the Horner-Emmons olefination of bis(tetrahydrofuran) aldehyde 53 and α-pyrone phosphonate 5. A key step features the stereoselective construction of a sterically congested quaternary center embedded in the densely functionalized bis(tetrahydrofuran) subunit by a Lewis acid-catalyzed, pinacol-type rearrangement of an epoxy silyl ether. This pivotal rearrangement methodology parallels the proposed biosynthetic pathway of 1 and is ripe for applications to the stereocontrolled synthesis of structurally complex natural products.

Total synthesis of (±)-asteltoxin

A convergent synthesis of (±)-asteltoxin has been achieved in 16 steps (3.0% overall yield) from 3,4-dimethylfuran. The attachment of the triene pyrone side chain to the bis(tetrahydrofuran) skeleton proceeds by way of the addition of the Corey equivalent to anion 3 to the aldehyde 2 and a subsequent aldol condensation-dehydration reaction of pyrone 4.