(E)-(2S,3S)-2-Benzyloxy-3-((1S,2R)-2-benzyloxy-4-hydroxy-1-methoxy-butyl)-4-methyl-octa-4,7-dienoic acid methyl ester

Base Information

Chemical Name:(E)-(2S,3S)-2-Benzyloxy-3-((1S,2R)-2-benzyloxy-4-hydroxy-1-methoxy-butyl)-4-methyl-octa-4,7-dienoic acid methyl ester
CAS No.:192932-01-7
Molecular Formula:C₂₉H₃₈O₆
Molecular Weight:482.617
Hs Code.:

Synonyms:(E)-(2S,3S)-2-Benzyloxy-3-((1S,2R)-2-benzyloxy-4-hydroxy-1-methoxy-butyl)-4-methyl-octa-4,7-dienoic acid methyl ester

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Chemical Property of (E)-(2S,3S)-2-Benzyloxy-3-((1S,2R)-2-benzyloxy-4-hydroxy-1-methoxy-butyl)-4-methyl-octa-4,7-dienoic acid methyl ester

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Technology Process of (E)-(2S,3S)-2-Benzyloxy-3-((1S,2R)-2-benzyloxy-4-hydroxy-1-methoxy-butyl)-4-methyl-octa-4,7-dienoic acid methyl ester

There total 14 articles about (E)-(2S,3S)-2-Benzyloxy-3-((1S,2R)-2-benzyloxy-4-hydroxy-1-methoxy-butyl)-4-methyl-octa-4,7-dienoic acid methyl 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: 95.0%

: 192931-91-2
(E)-(2S,3S)-2-Benzyloxy-3-[(1S,2R)-2-benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-methoxy-butyl]-4-methyl-octa-4,7-dienoic acid methyl ester

: 192932-01-7
(E)-(2S,3S)-2-Benzyloxy-3-((1S,2R)-2-benzyloxy-4-hydroxy-1-methoxy-butyl)-4-methyl-octa-4,7-dienoic acid methyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4039(97)00925-8

Reference yield:

: 18968-50-8,29587-02-8,32166-85-1,36215-54-0,43138-65-4,65725-74-8,67816-77-7
1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol

: 192932-01-7
(E)-(2S,3S)-2-Benzyloxy-3-((1S,2R)-2-benzyloxy-4-hydroxy-1-methoxy-butyl)-4-methyl-octa-4,7-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: TEA / CH₂Cl₂ / 0.5 h / -30 - -20 °C

2: NaI / butan-2-one / 9 h / 100 °C

3: 1.) 9-BBN; 2.) 30percent H₂O₂, 3N NaOH / 1.) THF, -40 deg C to r.t., overnight; 2.) 60-70 deg C, 2 h

4: Dowex 50x2-200 resin / H₂O / 1 h / 100 °C

5: 1.) NaIO₄; 3.) K₂CO₃ / 1.) Me₂CO, H₂O, r.t., 2 h; 2.) MeCN, 100-110 deg C, 20 h; 3.) MeOH, r.t., 4 h

6: 93 percent / DMAP, TEA / CH₂Cl₂ / Ambient temperature

7: CF₃SO₃H / cyclohexane; CH₂Cl₂ / Ambient temperature

8: DIBALH / toluene / 1.5 h / -78 °C

9: 90 percent / MnO₂ / CCl₄ / Ambient temperature

10: tetrahydrofuran / 1 h / -78 - 0 °C

11: 100 percent / DMAP, DCC / CH₂Cl₂ / 2 h / Ambient temperature

12: 1.) LHMDS, TMSCl, TEA; 2.) Triton B / 1.) THF, -78 deg C to r.t., overnight; 2.) THF, r.t., 2 h

13: 95 percent / (n-Bu)4NF / tetrahydrofuran / Ambient temperature

With dmap; manganese(IV) oxide; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; trifluorormethanesulfonic acid; Dowex 50x2-200 resin; TEA; tetrabutyl ammonium fluoride; dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide; diisobutylaluminium hydride; potassium carbonate; dicyclohexyl-carbodiimide; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; tetrachloromethane; dichloromethane; cyclohexane; water; toluene; butanone;
DOI:10.1016/S0040-4039(97)00925-8

Reference yield:

: 32166-82-8
Methanesulfonic acid (R)-2-methanesulfonyloxy-1-((3aR,5S,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester

: 192932-01-7
(E)-(2S,3S)-2-Benzyloxy-3-((1S,2R)-2-benzyloxy-4-hydroxy-1-methoxy-butyl)-4-methyl-octa-4,7-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: NaI / butan-2-one / 9 h / 100 °C

2: 1.) 9-BBN; 2.) 30percent H₂O₂, 3N NaOH / 1.) THF, -40 deg C to r.t., overnight; 2.) 60-70 deg C, 2 h

3: Dowex 50x2-200 resin / H₂O / 1 h / 100 °C

4: 1.) NaIO₄; 3.) K₂CO₃ / 1.) Me₂CO, H₂O, r.t., 2 h; 2.) MeCN, 100-110 deg C, 20 h; 3.) MeOH, r.t., 4 h

5: 93 percent / DMAP, TEA / CH₂Cl₂ / Ambient temperature

6: CF₃SO₃H / cyclohexane; CH₂Cl₂ / Ambient temperature

7: DIBALH / toluene / 1.5 h / -78 °C

8: 90 percent / MnO₂ / CCl₄ / Ambient temperature

9: tetrahydrofuran / 1 h / -78 - 0 °C

10: 100 percent / DMAP, DCC / CH₂Cl₂ / 2 h / Ambient temperature

11: 1.) LHMDS, TMSCl, TEA; 2.) Triton B / 1.) THF, -78 deg C to r.t., overnight; 2.) THF, r.t., 2 h

12: 95 percent / (n-Bu)4NF / tetrahydrofuran / Ambient temperature

With dmap; manganese(IV) oxide; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; trifluorormethanesulfonic acid; Dowex 50x2-200 resin; TEA; tetrabutyl ammonium fluoride; dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide; diisobutylaluminium hydride; potassium carbonate; dicyclohexyl-carbodiimide; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; tetrachloromethane; dichloromethane; cyclohexane; water; toluene; butanone;
DOI:10.1016/S0040-4039(97)00925-8