(S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanoic acid methoxy-methyl-amide

Base Information

Chemical Name:(S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanoic acid methoxy-methyl-amide
CAS No.:194342-82-0
Molecular Formula:C₁₉H₂₈BrNO₅
Molecular Weight:430.339
Hs Code.:

Synonyms:(S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanoic acid methoxy-methyl-amide

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Chemical Property of (S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanoic acid methoxy-methyl-amide

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Technology Process of (S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanoic acid methoxy-methyl-amide

There total 6 articles about (S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanoic acid methoxy-methyl-amide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

: 110-87-2
3,4-dihydro-2H-pyran

: 194342-73-9
(S)-5-(2-Bromo-benzyloxy)-3-hydroxy-pentanoic acid methoxy-methyl-amide

: 194342-82-0
(S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanoic acid methoxy-methyl-amide

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; for 18h; Ambient temperature;
DOI:10.1016/S0040-4039(97)01140-4

Reference yield:

: 18982-54-2
o-bromobenzyl alcohol

: 194342-82-0
(S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature

2: 1.) 9-BBN; 2.) NaOH, H₂O₂ / 1.) THF, irrad., r.t., 3 h; 2.) reflux, 1 h

3: 76 percent / PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

4: 83 percent / 1.) Sn(OTf)2, N-ethylpiperidine / CH₂Cl₂ / 1.) -50 deg C to -40 deg C, 4 h; 2.) -78 deg C, 4 h

5: 94 percent / Me₃Al / toluene; CH₂Cl₂ / -25 - 0 °C

6: 97 percent / PPTS / CH₂Cl₂ / 18 h / Ambient temperature

With 1-ethyl-piperidine; sodium hydroxide; tin(II) trifluoromethanesulfonate; 9-borabicyclo[3.3.1]nonane dimer; Celite; dihydrogen peroxide; trimethylaluminum; pyridinium p-toluenesulfonate; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/S0040-4039(97)01140-4

Reference yield:

: 87280-01-1
1-((allyloxy)methyl)-2-bromobenzene

: 194342-82-0
(S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 9-BBN; 2.) NaOH, H₂O₂ / 1.) THF, irrad., r.t., 3 h; 2.) reflux, 1 h

2: 76 percent / PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

3: 83 percent / 1.) Sn(OTf)2, N-ethylpiperidine / CH₂Cl₂ / 1.) -50 deg C to -40 deg C, 4 h; 2.) -78 deg C, 4 h

4: 94 percent / Me₃Al / toluene; CH₂Cl₂ / -25 - 0 °C

5: 97 percent / PPTS / CH₂Cl₂ / 18 h / Ambient temperature

With 1-ethyl-piperidine; sodium hydroxide; tin(II) trifluoromethanesulfonate; 9-borabicyclo[3.3.1]nonane dimer; Celite; dihydrogen peroxide; trimethylaluminum; pyridinium p-toluenesulfonate; pyridinium chlorochromate; In dichloromethane; toluene;
DOI:10.1016/S0040-4039(97)01140-4