Benzoic acid (1R,2R,3S)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-methyl-pent-4-enyl ester

Base Information

Chemical Name:Benzoic acid (1R,2R,3S)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-methyl-pent-4-enyl ester
CAS No.:200186-35-2
Molecular Formula:C₂₂H₂₆O₅
Molecular Weight:370.445
Hs Code.:

Synonyms:Benzoic acid (1R,2R,3S)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-methyl-pent-4-enyl ester

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Chemical Property of Benzoic acid (1R,2R,3S)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-methyl-pent-4-enyl ester

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Technology Process of Benzoic acid (1R,2R,3S)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-methyl-pent-4-enyl ester

There total 2 articles about Benzoic acid (1R,2R,3S)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-methyl-pent-4-enyl 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: 80.0%

: 65-85-0,8013-63-6
benzoic acid

: [(2S,3R)-3-((1R,2S)-1-Benzyloxy-2-methyl-but-3-enyl)-oxiranyl]-methanol

: 200186-35-2
Benzoic acid (1R,2R,3S)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-methyl-pent-4-enyl ester

Guidance literature:: With titanium(IV) isopropylate; In tetrahydrofuran;
DOI:10.1016/S0040-4039(97)10499-3

Reference yield:

: 200186-34-1
C₁₅H₂₀O₃

: 65-85-0,8013-63-6
benzoic acid

: 200186-35-2
Benzoic acid (1R,2R,3S)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-methyl-pent-4-enyl ester

Guidance literature:: C₁₅H₂₀O₃; benzoic acid; With titanium(IV) isopropylate; In dichloromethane; for 50h; Inert atmosphere;

With citric acid; In diethyl ether; water; for 1h; regioselective reaction;
DOI:10.1016/j.tet.2009.04.001

Reference yield:

: 200186-35-2
Benzoic acid (1R,2R,3S)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-methyl-pent-4-enyl ester

: 200186-49-8
C₄₉H₉₂O₁₀Si₃

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) Hg(OAc)2; 2.) Et₃N, DMAP; 3.) O₂, NaBH₄ / 1.) THF; 2.) CH₂Cl₂; 3.) DMF, CH₂Cl₂

2: 94 percent / NaOMe / methanol

3: 78 percent / TsOH / benzene / Heating

4: 92 percent / Swern oxidation

5: n-BuLi, HMPA / diethyl ether / -50 °C

6: 98 percent / 2,6-lutidine / CH₂Cl₂

7: 88 percent / TFA / CH₂Cl₂; H₂O / -10 °C

8: Hg(ClO₄)2, 2,6-lutidine / tetrahydrofuran / 0 °C

9: pyr

10: 56 percent / TMEDA / hexamethylphosphoric acid triamide / 80 °C

11: 78 percent / H₂, CaCO₃ / Pd/C / ethanol; ethyl acetate

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; n-butyllithium; mercury(II) perchlorate; N,N,N,N,-tetramethylethylenediamine; mercury(II) diacetate; hydrogen; oxygen; sodium methylate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; calcium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1016/S0040-4039(97)10499-3