62948-37-2

Basic information

• Product Name: Dispiro[oxirane-2,3'(2'H)-benzofuran-2',2''-[2H]- pyran]-6'-carboxylic acid,decahydro-5''-methyl-4''-[[(2E)-1-oxo- 3-phenyl-2-propenyl]oxy]-,methyl ester,(2R,2'S,3'aS,4''R,5''S,6'S,7'aR)-
• CAS NO: 62948-37-2
• Molecular Formula: C₂₅H₃₀O₇
• Molecular Weight: 442.509
• Mol File: 62948-37-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Dispiro[oxirane-2,3'(2'H)-benzofuran-2',2''-[2H]- pyran]-6'-carboxylic acid,decahydro-5''-methyl-4''-[[(2E)-1-oxo- 3-phenyl-2-propenyl]oxy]-,methyl ester,(2R,2'S,3'aS,4''R,5''S,6'S,7'aR)- (CAS DataBase Reference)
• NIST Chemistry Reference: Dispiro[oxirane-2,3'(2'H)-benzofuran-2',2''-[2H]- pyran]-6'-carboxylic acid,decahydro-5''-methyl-4''-[[(2E)-1-oxo- 3-phenyl-2-propenyl]oxy]-,methyl ester,(2R,2'S,3'aS,4''R,5''S,6'S,7'aR)- (62948-37-2)
• EPA Substance Registry System: Dispiro[oxirane-2,3'(2'H)-benzofuran-2',2''-[2H]- pyran]-6'-carboxylic acid,decahydro-5''-methyl-4''-[[(2E)-1-oxo- 3-phenyl-2-propenyl]oxy]-,methyl ester,(2R,2'S,3'aS,4''R,5''S,6'S,7'aR)- (62948-37-2)

Safety Data

• Hazardous Substances Data: 62948-37-2(Hazardous Substances Data)

Upstream product

• 109586-32-5 methyl (1R,3S,6S)-7-acetyl-9-oxa-8-azabicyclo<4.3.0>non-7-ene-3-carboxylate 
• 109586-31-4 methyl (1S,2R,4S,6R)-9-acetyl-2-hydroxy-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate 
• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 119680-64-7 methyl (1S,2R,4S,6R)-9-acetyl-2-<(phenoxythionocarbonyl)oxy>-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate 
• 82167-79-1 (-)-(R)-4-benzyloxy-3-methylbutan-2-one 
• 88670-92-2 (SR)-2-hydroxy-2-((S)-4-(prop-1-en-2-yl)cyclohex-1-enyl)acetonitrile 
• 82189-55-7 (S)-2,3-dimethyl-3-buten-1-ol 
• 82167-80-4 (3R,3aS,6S,7aR)-3-Benzyloxymethoxy-3-benzyloxymethyl-2-((S)-4-hydroxy-3-methyl-2-methylene-butyl)-6-vinyl-octahydro-benzofuran-2-ol 
• 82167-72-4 (3R,3aS,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>hexahydro-6-vinyl-2(3H)-benzofuranone 
• 88670-93-3 (1S,2S,4S)-7-<(benzyloxy)methoxy>-2,9-dihydroxy-p-methane-7-carbonitrile 
• 82167-73-5 (4S)-7-<(benzyloxy)methoxy>-p-mentha-1,8-diene-7-carbonitrile 
• 88671-03-8 (S)-4-(benzyloxy)-2,3-dimethyl-1-butene 
• 82167-84-8 C₁₆H₂₂O₆ 
• 82167-83-7 C₁₅H₂₀O₆ 

Relevant articles and documents

Phyllanthoside-Phyllanthostatin Synthetic Studies. 7. Total Synthesis of (+)-Phyllanthocin and (+)-Phyllanthocindiol

A stereochemically linear total synthesis of (+)-phyllanthocin (5a), the aglycon methyl ester of the antineoplastic glycoside (+)-phyllanthoside (1), is described. The synthesis proceeds in 23 steps (4.5% overall yield) and affords (+)-phyllanthocin in high enantiomeric purity. The central features of the strategy include: (a) construction of aldehyde 8 via a stereoselective, intramolecular ene reaction; (b) elaboration of the spiroketal unit by a two-step tactic involving addition of a functionalized dihydropyran anion (i.e., 9) to 8, followed by a highly stereoselective spiroketalization; and (c) chemo- and stereoselective methylenation of the C(7) carbonyl group. In addition, a second-generation approach is presented, wherein an augmented spiroketalization maneuver not only establishes the C(8) spirocenter but also permits the regio- and stereocontrolled introduction of the C(11) methyl group. The latter sequence furnishes (+)-phyllanthocin in 21 steps (5.6% overall yield). Finally, the advanced phyllanthocin intermediate (+)-49 is converted in five steps (42% overall yield) to (+)-phyllanthocindiol (5b), the aglycon of phyllanthostatin 3.

Application of nitrile oxide cycloadditions to a convergent, assymmetric synthesis of (+)-phyllanthocin

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TOTAL SYNTHESIS OF ( plus )-PHYLLANTHOCIN.

Investigations culminating in the total synthesis of ( plus )-phyllanthocin via a highly convergent route beginning with natural tartaric acid are reported. The stereochemical consequences of internal spiroketalization with protic acid and Lewis acid chel