1353566-58-1

Basic information

• Product Name: (2R)-2-(benzyloxy)-5-hexenoic acid
• Synonyms: (2R)-2-(benzyloxy)-5-hexenoic acid
• CAS NO: 1353566-58-1
• Molecular Weight: 220.268
• Mol File: 1353566-58-1.mol

Chemical Properties

• CAS DataBase Reference: (2R)-2-(benzyloxy)-5-hexenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-(benzyloxy)-5-hexenoic acid(1353566-58-1)
• EPA Substance Registry System: (2R)-2-(benzyloxy)-5-hexenoic acid(1353566-58-1)

Safety Data

• Hazardous Substances Data: 1353566-58-1(Hazardous Substances Data)

Upstream product

• 147973-69-1 (R)-2-benzyloxyhex-5-enal 
• 1387444-54-3 (2R,3R)-3-O-benzylhept-6-ene-1,2,3-triol 
• 1387444-56-5 (2R,3R)-1,2-O-cyclohexylidene-3-O-benzylhept-6-ene-1,2,3-triol 
• 113730-86-2 (2R,3R)-1,2-(cyclohexylidenedioxy)hept-6-en-3-ol 
• 83861-87-4 (2R)-2-(benzyloxy)-5-hexen-1-ol 
• 100-39-0 benzyl bromide 
• 1335029-07-6 (R)-1-(((2-(benzyloxy)hex-5-en-1-yl)oxy)methyl)-4-methoxybenzene 
• 1012367-43-9 (R)-1-(4-Methoxy-benzyloxy)-hex-5-en-2-ol 

Downstream Products

• 1353566-64-9 (1R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]butyl (2R)-2-(benzyloxy)-5-hexenoate 
• 1353566-59-2 C₂₂H₃₀O₅ 
• 1363407-74-2 C₂₂H₃₀O₅ 
• 1353566-66-1 (1S)-1-[(4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]butyl (2R)-2-(benzyloxy)-5-hexenoate 
• 1387444-55-4 (4R,5R,6S)-5,6-dibenzyloxyoct-7-en-4-yl (2R)-2-benzyloxyhex-5-enoate 

Relevant articles and documents

Formal and total syntheses of herbarumin i and II, respectively from (R)-2,3-cyclohexylideneglyceraldehyde

Vinyl Grignard addition to 2, obtained via a nitroaldol reaction of (R)-2,3-cyclohexylideneglyceraldehyde 1, afforded 3 with absolute stereoselectivity. This was transformed into 7, a known intermediate for the formal synthesis of herbarumin I A. Condensation of 7 with 10, another intermediate obtained from 1 afforded 11. The RCM reaction of 11 in the presence of Grubbs second generation catalyst Ru II and global debenzylation of the product in the presence of TiCl4 furnished B. The efficacy of the entire route was due to its operational simplicity, the easy accessibility of 1, all of the reactions being inexpensive and the high stereoselectivity of the asymmetric C-C bond forming reactions involved, as well as E-selectivity of the RCM reaction.

Titanium(IV)-promoted regioselective nucleophilic ring-opening reaction of chiral epoxyallyl alcohols with acids as a tool for ready access to chiral 1,2,3-triol monoesters: Application to stereoselective total synthesis of macrolides

Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.