(E)-(2S,3S)-2-Benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dimethyl-non-4-enoic acid methyl ester

Base Information

Chemical Name:(E)-(2S,3S)-2-Benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dimethyl-non-4-enoic acid methyl ester
CAS No.:863453-53-6
Molecular Formula:C₂₅H₃₈O₆
Molecular Weight:434.573
Hs Code.:

Synonyms:(E)-(2S,3S)-2-Benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dimethyl-non-4-enoic acid methyl ester

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Chemical Property of (E)-(2S,3S)-2-Benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dimethyl-non-4-enoic acid methyl ester

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Technology Process of (E)-(2S,3S)-2-Benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dimethyl-non-4-enoic acid methyl ester

There total 10 articles about (E)-(2S,3S)-2-Benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dimethyl-non-4-enoic 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: 80.0%

: 863453-39-8
(E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl ester

: 863453-53-6
(E)-(2S,3S)-2-Benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dimethyl-non-4-enoic acid methyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1016/j.bmcl.2005.05.065

Reference yield:

: 863453-34-3
(E)-3-((4S,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-acrylic acid methyl ester

: 863453-53-6
(E)-(2S,3S)-2-Benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dimethyl-non-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C

2.1: 96 percent / DIBAL-H / CH₂Cl₂ / 4 h / -78 °C

3.1: 91 percent / MnO₂ / CH₂Cl₂ / 20 h / 20 °C

4.1: 25 percent / tetrahydrofuran / 1 h / -78 °C

5.1: 82 percent / PPh₃; DIAD / tetrahydrofuran / 3.5 h / 0 - 20 °C

6.1: LiHMDS; TMSCl; Et₃N / tetrahydrofuran / 11 h / -78 - 20 °C

6.2: 70 percent / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C

7.1: 80 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

With 1H-imidazole; manganese(IV) oxide; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 5.1: Mitsunobu reaction / 6.1: Ireland-Claisen rearrangement;
DOI:10.1016/j.bmcl.2005.05.065

Reference yield:

: 863453-35-4
(E)-3-[(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-methyl-propenal

: 863453-53-6
(E)-(2S,3S)-2-Benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dimethyl-non-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 25 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 82 percent / PPh₃; DIAD / tetrahydrofuran / 3.5 h / 0 - 20 °C

3.1: LiHMDS; TMSCl; Et₃N / tetrahydrofuran / 11 h / -78 - 20 °C

3.2: 70 percent / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C

4.1: 80 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

With chloro-trimethyl-silane; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; 2.1: Mitsunobu reaction / 3.1: Ireland-Claisen rearrangement;
DOI:10.1016/j.bmcl.2005.05.065