169900-77-0

Basic information

• Product Name: 5-benzyloxy-2(Z)-pentenoic acid methyl ester
• Synonyms: 5-benzyloxy-2(Z)-pentenoic acid methyl ester
• CAS NO: 169900-77-0
• Molecular Weight: 220.268
• Mol File: 169900-77-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-benzyloxy-2(Z)-pentenoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-benzyloxy-2(Z)-pentenoic acid methyl ester(169900-77-0)
• EPA Substance Registry System: 5-benzyloxy-2(Z)-pentenoic acid methyl ester(169900-77-0)

Safety Data

• Hazardous Substances Data: 169900-77-0(Hazardous Substances Data)

Upstream product

• 19790-60-4 3-Benzyloxypropanal 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 4799-68-2 3-benzyloxypropan-1-ol 
• 70388-33-9 4-benzyloxybut-1-ene 
• 115384-91-3 bis(2,2,2-trifluoroethyl)(methoxy)carbonylmethylphosphonate 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 

Downstream Products

• 179927-66-3 (4R,5S)-(+)-(5-benzyloxy-2-(Z)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone 
• 179927-67-4 (4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone 
• 179927-65-2 5-O-benzyl-2-deoxy-2-fluoro-L-γ-xylonic lactone 
• 179927-64-1 5-O-benzyl-2-deoxy-2-fluoro-D-γ-xylonic lactone 
• 179927-68-5 5-benzyloxy-2-(Z)-pentenoic acid 

Relevant articles and documents

Application of oxazolidinone α-fluoro amide chiral building blocks in the asymmetric synthesis of fluorinated carbohydrates: 2-Deoxy-2-fluoropentoses

Deconjugative electrophilic fluorination of the lithium dienolate of Z-α,β-unsaturated imide (+)-9 with N-fluorobenzene-sulfonimide (NFSi) afforded the E-β,γ-unsaturated α-fluoro imide (+)-10 as a single diastereoisomer. Dihydroxylation resulted in the formation of 2-fluoro-2-deoxy-γ-xylonic and -lyxonic lactones, 12a and 12b, respectively. Reduction and deprotection of the lactones afforded 2-deoxy-2-fluoro-xylo-D-pyranose (15) and 2-deoxy-2-fluoro-lyxo-L-pyranose (17). (C) 2000 Elsevier Science Ltd.

Asymmetric synthesis of 2-deoxy-2-fluoro-γ-aldonolactones and their conversion to 2-deoxy-2-fluoropentoses

2-Fluoro-2-deoxy-γ-xylonic and -lyxonic lactones, 7a and 7b, were prepared via the diastereoselective fluorination of the α,β-unsaturated chiral imide 5 followed by dihydroxylation. Lactones 7a and 7b were converted to 2-deoxy-2-fluoro-xylo-D-pyranose (1) and 2-deoxy-2-fluoro-lyxo-L-pyranose (2) by reduction and deprotection.