Benzoic acid (2S,3R,5S)-5-((S)-3-benzyloxy-1-bromo-propyl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Benzoic acid (2S,3R,5S)-5-((S)-3-benzyloxy-1-bromo-propyl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester
CAS No.:119343-26-9
Molecular Formula:C₂₂H₂₅BrO₅
Molecular Weight:449.341
Hs Code.:

Synonyms:Benzoic acid (2S,3R,5S)-5-((S)-3-benzyloxy-1-bromo-propyl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

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Chemical Property of Benzoic acid (2S,3R,5S)-5-((S)-3-benzyloxy-1-bromo-propyl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

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Technology Process of Benzoic acid (2S,3R,5S)-5-((S)-3-benzyloxy-1-bromo-propyl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

There total 12 articles about Benzoic acid (2S,3R,5S)-5-((S)-3-benzyloxy-1-bromo-propyl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester 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:

: 22273-77-4
((but-3-yn-1-yloxy)methyl)benzene

: 119343-26-9
Benzoic acid (2S,3R,5S)-5-((S)-3-benzyloxy-1-bromo-propyl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) n-BuLi / 1.) THF, -80 deg C, 10 min, 2.) -80 deg C, then room temperature

2: 87 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

4: LiBr / dimethylformamide / 0.33 h / 0 °C

5: HMPTA / tetrahydrofuran / 10 h / 1.) -60 deg C, 2.) room temperature

6: MeOH, HCl

7: 85 percent / LiAlH₄ / diethyl ether / 12 h / 1.) 0 deg C, 2.) 20 deg C

8: 88 percent / L-(+)-diethyl tartrate, (CH₃)3COOH, molecular sieves 3 Angstroem / CH₂Cl₂ / 2 h / -20 °C

9: titanium tetraisopropoxide / CH₂Cl₂ / 0.5 h / Ambient temperature

10: imidazole / dimethylformamide / 12 h / 25 °C

11: 92 percent / 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TBCD) / tetrahydrofuran; hexamethylphosphoric acid triamide / -60 °C / further reagent

12: n-Bu₄NF / tetrahydrofuran

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; diethyl (2R,3R)-tartrate; 3 A molecular sieve; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; tetrabutyl ammonium fluoride; triethylamine; lithium bromide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(88)85109-8

Reference yield:

: 22273-79-6
5-benzyloxy-2-pentyn-1-ol

: 119343-26-9
Benzoic acid (2S,3R,5S)-5-((S)-3-benzyloxy-1-bromo-propyl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 87 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

3: LiBr / dimethylformamide / 0.33 h / 0 °C

4: HMPTA / tetrahydrofuran / 10 h / 1.) -60 deg C, 2.) room temperature

5: MeOH, HCl

6: 85 percent / LiAlH₄ / diethyl ether / 12 h / 1.) 0 deg C, 2.) 20 deg C

7: 88 percent / L-(+)-diethyl tartrate, (CH₃)3COOH, molecular sieves 3 Angstroem / CH₂Cl₂ / 2 h / -20 °C

8: titanium tetraisopropoxide / CH₂Cl₂ / 0.5 h / Ambient temperature

9: imidazole / dimethylformamide / 12 h / 25 °C

10: 92 percent / 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TBCD) / tetrahydrofuran; hexamethylphosphoric acid triamide / -60 °C / further reagent

11: n-Bu₄NF / tetrahydrofuran

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; tetrabutyl ammonium fluoride; triethylamine; lithium bromide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(88)85109-8

Reference yield:

: 119343-21-4
[(2S,3S)-3-((E)-5-Benzyloxy-pent-2-enyl)-oxiranyl]-methanol

: 119343-26-9
Benzoic acid (2S,3R,5S)-5-((S)-3-benzyloxy-1-bromo-propyl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: titanium tetraisopropoxide / CH₂Cl₂ / 0.5 h / Ambient temperature

2: imidazole / dimethylformamide / 12 h / 25 °C

3: 92 percent / 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TBCD) / tetrahydrofuran; hexamethylphosphoric acid triamide / -60 °C / further reagent

4: n-Bu₄NF / tetrahydrofuran

With 1H-imidazole; titanium(IV) isopropylate; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(88)85109-8