929118-02-5

Basic information

• Product Name: (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid
• Synonyms: (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid
• CAS NO: 929118-02-5
• Molecular Weight: 486.56
• Mol File: 929118-02-5.mol

Chemical Properties

• CAS DataBase Reference: (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid(929118-02-5)
• EPA Substance Registry System: (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid(929118-02-5)

Safety Data

• Hazardous Substances Data: 929118-02-5(Hazardous Substances Data)

Upstream product

• 460348-12-3 (R)-5-(trimethylsilyl)pent-4-yn-2-ol 
• 148516-13-6 (S)-1-chloro-2-hydroxy-5-trimethylsilyl-4-pentyne 
• 929117-83-9 (S,Z)-3-bromo-1-(2-tert-butyldiphenylsilyloxy)ethyl-2-propenyl acetate 
• 1053723-00-4 C₂₆H₃₉O₄Si₂Br 
• 929117-82-8 C₂₆H₃₈O₄Si₂ 
• 851278-46-1 (1R,2R,3R)-5-(tert-butyldiphenylsilyloxy)-1,2-epoxy-1-trimethylsilylpentan-3-ol 
• 851278-49-4 (3S,4S,5E,7S,9R)-1-[(tert-butyldiphenylsilyl)oxy]-9-[(4-methoxybenzyl)oxy]-3,4,7-tri[(methoxymethyl)oxy]-5-decene 
• 851278-41-6 (3S,4R,5S,6E)-1-(tert-butyldiphenylsilyloxy)-4,5-epoxy-9-(4-methoxybenzyloxy)-6-decen-3-ol 
• 851278-40-5 (3S,4Z,6E,9R)-1-[(tert-butyldiphenylsilyl)oxy]-9-[(4-methoxybenzyl)oxy]-4,6-decadien-3-ol 
• 851278-45-0 (1E)-5-[(tert-butyldiphenylsilyl)oxy]-1-trimethylsilyl-1-penten-3-ol 
• 851278-57-4 (1E,3S)-5-[(tert-butyldiphenylsilyl)oxy]-1-trimethylsilyl-1-penten-3-ol 
• 851278-44-9 (1Z,3S)-1-bromo-5-[(tert-butyldiphenylsilyl)oxy]-1-penten-3-ol 
• 851278-43-8 (1'E,4'R)-2-[4'-(4-methoxybenzyloxy)-1'-pentenyl]-5,5-dimethyl-1,3,2-dioxaborinane 
• 603040-81-9 (R)-1-methoxy-4-((pent-4-yn-2-yloxy)methyl)benzene 

Downstream Products

• 851278-51-8 methyl (3S,4S,5E,7S,9R)-9-[(4-methoxybenzyl)oxy]-3,4,7-tri[(methoxymethyl)oxy]-5-decenoate 
• 127393-89-9 (4S,5S,8S,10R,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one 

Relevant articles and documents

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.

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