(4R,5S,6R)-6-hydroxy-4,5-di-O-isopropylidene-7-trityloxy-heptanoic acid methyl ester

Base Information

Chemical Name:(4R,5S,6R)-6-hydroxy-4,5-di-O-isopropylidene-7-trityloxy-heptanoic acid methyl ester
CAS No.:941280-71-3
Molecular Formula:C₃₀H₃₄O₆
Molecular Weight:490.596
Hs Code.:

Synonyms:(4R,5S,6R)-6-hydroxy-4,5-di-O-isopropylidene-7-trityloxy-heptanoic acid methyl ester

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Chemical Property of (4R,5S,6R)-6-hydroxy-4,5-di-O-isopropylidene-7-trityloxy-heptanoic acid methyl ester

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Technology Process of (4R,5S,6R)-6-hydroxy-4,5-di-O-isopropylidene-7-trityloxy-heptanoic acid methyl ester

There total 1 articles about (4R,5S,6R)-6-hydroxy-4,5-di-O-isopropylidene-7-trityloxy-heptanoic 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: 94.0%

: 3-[5-(1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid methyl ester

: 941280-71-3
(4R,5S,6R)-6-hydroxy-4,5-di-O-isopropylidene-7-trityloxy-heptanoic acid methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 1h;
DOI:10.1016/j.tet.2007.03.047

Reference yield:

: 941280-71-3
(4R,5S,6R)-6-hydroxy-4,5-di-O-isopropylidene-7-trityloxy-heptanoic acid methyl ester

: (2S,3S,4R)-2-azido-10-bromo-3,4-di-O-isopropylidene-1-trityloxy-dec-7-ene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -40 °C

2.1: 1.39 g / tetramethylguanidinium azide / CH₂Cl₂ / -40 - 20 °C

3.1: 70 percent / diisobutylaluminium hydride / toluene / 6 h / -78 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C

4.2: 57 percent / tetrahydrofuran / 0 - 20 °C

5.1: 56 percent / Grubbs' second generation / CH₂Cl₂ / 18 h / 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; tetramethylguanidinum azide; lithium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; toluene; 4.1: Wittig reaction / 4.2: Wittig reaction;
DOI:10.1016/j.tet.2007.03.047

Reference yield:

: 941280-71-3
(4R,5S,6R)-6-hydroxy-4,5-di-O-isopropylidene-7-trityloxy-heptanoic acid methyl ester

: 4-(1-azido-2-trityloxy-ethyl)-2,2-dimethyl-5-(6-phenyl-hex-3-enyl)-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -40 °C

2.1: 1.39 g / tetramethylguanidinium azide / CH₂Cl₂ / -40 - 20 °C

3.1: 70 percent / diisobutylaluminium hydride / toluene / 6 h / -78 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C

4.2: 57 percent / tetrahydrofuran / 0 - 20 °C

5.1: 57 percent / Grubbs' second generation / CH₂Cl₂ / 18 h / 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; tetramethylguanidinum azide; lithium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; toluene; 4.1: Wittig reaction / 4.2: Wittig reaction;
DOI:10.1016/j.tet.2007.03.047