851278-45-0

Basic information

• Product Name: 1-Penten-3-ol, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-(trimethylsilyl)-, (1E)-
• CAS NO: 851278-45-0
• Molecular Formula: C24H36O2Si2
• Molecular Weight: 412.72
• Mol File: 851278-45-0.mol

Chemical Properties

• CAS DataBase Reference: 1-Penten-3-ol, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-(trimethylsilyl)-, (1E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Penten-3-ol, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-(trimethylsilyl)-, (1E)-(851278-45-0)
• EPA Substance Registry System: 1-Penten-3-ol, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-(trimethylsilyl)-, (1E)-(851278-45-0)

Safety Data

• Hazardous Substances Data: 851278-45-0(Hazardous Substances Data)

Upstream product

• 58207-97-9 tributyl[(E)-2-trimethylsilylethenyl]stannane 
• 112897-03-7 3-(tert-butyldiphenylsilyloxy)-1-propanal 

Downstream Products

• 851278-57-4 (1E,3S)-5-[(tert-butyldiphenylsilyl)oxy]-1-trimethylsilyl-1-penten-3-ol 
• 851278-46-1 (1R,2R,3R)-5-(tert-butyldiphenylsilyloxy)-1,2-epoxy-1-trimethylsilylpentan-3-ol 
• 851278-44-9 (1Z,3S)-1-bromo-5-[(tert-butyldiphenylsilyl)oxy]-1-penten-3-ol 
• 929118-00-3 2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol 
• 929117-87-3 (3S,4S,5E,7S,9R)-9-[(4-methoxybenzyl)oxy]-3,4,7-tri[(methoxymethyl)oxy]-5-decen-1-ol 
• 851278-51-8 methyl (3S,4S,5E,7S,9R)-9-[(4-methoxybenzyl)oxy]-3,4,7-tri[(methoxymethyl)oxy]-5-decenoate 
• 929118-02-5 (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid 
• 851278-40-5 (3S,4Z,6E,9R)-1-[(tert-butyldiphenylsilyl)oxy]-9-[(4-methoxybenzyl)oxy]-4,6-decadien-3-ol 
• 851278-41-6 (3S,4R,5S,6E)-1-(tert-butyldiphenylsilyloxy)-4,5-epoxy-9-(4-methoxybenzyloxy)-6-decen-3-ol 
• 929117-86-2 (E)-(3S,4S,7S,9R)-1-(tert-Butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-ene-3,4,7-triol 
• 929117-85-1 (E)-(3S,5R)-1-{(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-(4-methoxy-benzyloxy)-hex-1-en-3-ol 
• 851278-42-7 (1S,2E,4S,5S,2'R)-7-[(tert-butyldiphenylsilyl)oxy]-4,5-dihydroxy-1-[2'-[(4-methoxybenzyl)oxy]propyl]-2-heptenyl acetate 
• 929117-81-7 (3S,4S,5E,7S,9R)-1-(tert-butyldiphenylsilyloxy)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decene 
• 929117-84-0 Acetic acid (1S,3R)-1-((E)-2-{(4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-(4-methoxy-benzyloxy)-butyl ester 

Relevant articles and documents

Stereoselective synthesis of decarestrictine D from a previously inaccessible (2Z,4E)-alkadienyl alcohol precursor

(Chemical Equation Presented) The core structure of decarestrictine D was constructed by stereoselective oxygenation of (2Z,4E)-alkadienyl alcohol, which could be synthesized by a nickel-catalyzed coupling reaction between the corresponding cis bromide an

Nickel-catalyzed coupling producing (2Z)-2,4-alkadien-1-ols, conversion to (E)-3-alkene-1,2,5-triol derivatives, and synthesis of decarestrictine D

The 3-alkene-1,2,5-triol structure is not only a major framework of biologically important molecules but also a new functional-group-rich unit for synthesis of polyols and sugars. A method furnishing such triol derivatives 8 was developed and successfully applied to synthesis of decarestrictine D (18). First, coupling reaction of the unprotected alcohols 2 with borates 4 was investigated to produce the dienyl alcohols 6 with NiCl2(dppf) in Et2O/THF (5:1) at room temperature. The hydroxyl-group-directed epoxidation of 6 followed by palladium-catalyzed reaction with AcOH (Scheme 1) furnished 3-alkene-1,2,5-triol derivatives 8. Since each step proceeded with high stereo- and regioselectivities, the stereochemistry of 8 has been correlated with the olefin geometry of 6. With the above transformation in mind, synthesis of the full carbon skeleton of decarestrictine D (18) could be designed easily and was completed successfully. Furthermore, a new seco acid 19b with the MOM protective group for the three hydroxyl groups was found to afford macrolide 48 in a yield higher than those reported previously.