471924-14-8

Basic information

• Product Name: (E)-(2R,3R)-6-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-2-(4-methoxy-benzyloxy)-5-methyl-hex-5-en-3-ol
• Synonyms: (E)-(2R,3R)-6-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-2-(4-methoxy-benzyloxy)-5-methyl-hex-5-en-3-ol
• CAS NO: 471924-14-8
• Molecular Weight: 895.378
• Mol File: 471924-14-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-(2R,3R)-6-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-2-(4-methoxy-benzyloxy)-5-methyl-hex-5-en-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(2R,3R)-6-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-2-(4-methoxy-benzyloxy)-5-methyl-hex-5-en-3-ol(471924-14-8)
• EPA Substance Registry System: (E)-(2R,3R)-6-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-2-(4-methoxy-benzyloxy)-5-methyl-hex-5-en-3-ol(471924-14-8)

Safety Data

• Hazardous Substances Data: 471924-14-8(Hazardous Substances Data)

Upstream product

• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 389123-35-7 {2-[(2S,6R)-6-((E)-2-Bromo-propenyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane 
• 389123-22-2 (2R,6R)-2-((E)-2-Bromo-propenyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-4-one 
• 389123-39-1 [(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene 
• 389123-37-9 5-{2-[(2S,6R)-6-((E)-2-Bromo-propenyl)-4-methylene-tetrahydro-pyran-2-yl]-ethanesulfonyl}-1-phenyl-1H-tetrazole 
• 389123-36-8 5-{2-[(2S,6R)-6-((E)-2-Bromo-propenyl)-4-methylene-tetrahydro-pyran-2-yl]-ethylsulfanyl}-1-phenyl-1H-tetrazole 
• 389123-40-4 (Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-en-1-ol 
• 389123-41-5 (Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enal 
• 389123-38-0 (Z)-(R)-6-Benzyloxy-5-hydroxy-3-methyl-hex-2-enoic acid ethyl ester 
• 389123-23-3 2-[(2S,6R)-6-((E)-2-Bromo-propenyl)-4-methylene-tetrahydro-pyran-2-yl]-ethanol 
• 389123-24-4 (Z)-(R)-6-Benzyloxy-3-methyl-hex-2-ene-1,5-diol 
• 197520-87-9 (R)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-ynoate 
• 152386-85-1 (1R,2S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)-2-((4-methoxybenzyl)oxy)ethan-1-ol 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 389123-49-3 (2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-5-[(R)-2-hydroxy-1-(4-methoxy-benzyloxy)-ethyl]-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one 
• 389123-18-6 (S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetic acid 
• 1054610-92-2 (S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide 
• 389123-51-7 (2Z,4E)-Hexa-2,4-dienoic acid [(S)-((2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-hydroxy-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl)-(4-methoxy-benzyloxy)-methyl]-amide 
• 389123-29-9 (2Z,4E)-Hexa-2,4-dienoic acid [(S)-((2E,8E,10Z,14E)-(1R,5R,17R)-3,11-dimethyl-19-methylene-7,13-dioxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl)-(4-methoxy-benzyloxy)-methyl]-amide 
• 389123-50-6 (2Z,4E)-Hexa-2,4-dienoic acid [(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide 
• 389123-27-7 [(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 389123-28-8 [[13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]heneicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-hexa-2,4-dienoyl-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 471924-01-3 (2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-5-[(R)-2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one 
• 471923-99-6 (diethoxy-phosphoryl)-acetic acid 4-{6-[4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-8-oxo-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester 
• 471923-97-4 (diethoxy-phosphoryl)-acetic acid 4-{6-[4-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester 

Relevant articles and documents

Total syntheses of (+)-zampanolide and (+)-dactylolide exploiting a unified strategy

The first total syntheses of (+)-zampanolide (1) and (+)-dactylolide (2), members of a new class of tumor cell growth inhibitory macrolides, have been achieved. Key features of the unified synthetic scheme included the stereocontrolled construction of the cis-2,6-disubstituted tetrahydropyran via a modified Petasis-Ferrier rearrangement, a highly convergent assembly of the macrocyclic domain, and, in the case of zampanolide, a Curtius rearrangement/acylation tactic to install the N-acyl hemiaminal. The complete relative and absolute stereochemistries for both (+)-zampanolide and (+)-dactylolide were also assigned, albeit tentatively in the case of (+)-zampanolide (1).