(4R,5S)-5-((R)-1-(benzyloxy)pent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

Base Information

Chemical Name:(4R,5S)-5-((R)-1-(benzyloxy)pent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide
CAS No.:1312103-53-9
Molecular Formula:C₂₀H₂₉NO₅
Molecular Weight:363.454
Hs Code.:

Synonyms:(4R,5S)-5-((R)-1-(benzyloxy)pent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

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Chemical Property of (4R,5S)-5-((R)-1-(benzyloxy)pent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

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Technology Process of (4R,5S)-5-((R)-1-(benzyloxy)pent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

There total 1 articles about (4R,5S)-5-((R)-1-(benzyloxy)pent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide 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: 71.0%

: 1053694-92-0
(4R,5S)-5-((R)-1-hydroxypent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

: 100-39-0
benzyl bromide

: 1312103-53-9
(4R,5S)-5-((R)-1-(benzyloxy)pent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

Guidance literature:: With silver(l) oxide; In toluene; for 12h; Reflux;
DOI:10.1016/j.tet.2011.03.102

Reference yield:

: 1312103-53-9
(4R,5S)-5-((R)-1-(benzyloxy)pent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

: C₁₉H₂₇NO₆

Guidance literature:: (4R,5S)-5-((R)-1-(benzyloxy)pent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide; With ozone; In methanol; dichloromethane; at -78 ℃;

With dimethylsulfide; In methanol; dichloromethane; at -78 - 0 ℃; for 1h;
DOI:10.1016/j.tet.2011.03.102

Reference yield:

: 1312103-53-9
(4R,5S)-5-((R)-1-(benzyloxy)pent-4-en-1-yl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

: (4R,5R)-4,5-Bis-benzyloxy-hept-6-enal

Guidance literature:: Multi-step reaction with 9 steps

1.1: ozone / methanol; dichloromethane / -78 °C

1.2: 1 h / -78 - 0 °C

2.1: sodium tetrahydroborate / methanol / 1 h / -78 °C

2.2: -78 °C

3.1: 1H-imidazole; dmap / dichloromethane / 2 h / Reflux

4.1: sodium tetrahydroborate / methanol / 2 h / 0 °C

4.2: 0 °C

5.1: 1H-imidazole; iodine; triphenylphosphine / toluene / 2 h / Reflux

6.1: zinc / ethanol / 5 h / Reflux

7.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / 0 °C

7.2: 2 h / 0 - 20 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

9.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / toluene / 2 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; iodine; sodium hydride; ozone; dimethyl sulfoxide; triphenylphosphine; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2011.03.102