benzyl benzyl((S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3((methoxymethoxy)methyl)but-3-enyl)carbamate

Base Information

Chemical Name:benzyl benzyl((S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3((methoxymethoxy)methyl)but-3-enyl)carbamate
CAS No.:1337557-52-4
Molecular Formula:C₂₉H₃₇NO₆
Molecular Weight:495.616
Hs Code.:

Synonyms:benzyl benzyl((S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3((methoxymethoxy)methyl)but-3-enyl)carbamate

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Chemical Property of benzyl benzyl((S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3((methoxymethoxy)methyl)but-3-enyl)carbamate

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Technology Process of benzyl benzyl((S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3((methoxymethoxy)methyl)but-3-enyl)carbamate

There total 12 articles about benzyl benzyl((S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3((methoxymethoxy)methyl)but-3-enyl)carbamate 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: 75.0%

: 1337557-51-3
benzyl benzyl((S)-1-((4S,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-((methoxymethoxy)methyl)but-3-en-1-yl)carbamate

: 1337557-52-4
benzyl benzyl((S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3((methoxymethoxy)methyl)but-3-enyl)carbamate

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 60 ℃; for 4h; Reflux;
DOI:10.1016/j.tetasy.2011.07.009

Reference yield:

: 1233851-81-4
(S)-N-benzyl-1-((4S,5S)-5-((R)-3,3-diethyl-8,8,9,9-tetramethyl-4,7-dioxa-3,8-disiladecan-5-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-amine

: 1337557-52-4
benzyl benzyl((S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3((methoxymethoxy)methyl)but-3-enyl)carbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / tetrahydrofuran; toluene; mineral oil / 1 h / 20 °C / Cooling with ice

2.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / -10 - 20 °C

2.2: 2 h / 0 - 20 °C

3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 5 h / 20 °C / Cooling with ice

4.1: triethylamine / dichloromethane / 3 h / 20 °C

5.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.5 h / -78 °C

6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C / Cooling with ice

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

8.1: 1H-imidazole; iodine; triphenylphosphine / toluene / 4 h / 60 °C / Reflux

With 1H-imidazole; dmap; sodium tetrahydroborate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; cerium(III) chloride heptahydrate; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; iodine; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene; mineral oil;
DOI:10.1016/j.tetasy.2011.07.009

Reference yield:

: 1233851-77-8
C₂₁H₃₅NO₄Si

: 1337557-52-4
benzyl benzyl((S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3((methoxymethoxy)methyl)but-3-enyl)carbamate

Guidance literature:: Multi-step reaction with 10 steps

1.1: zinc / tetrahydrofuran / -15 - 20 °C

2.1: 1H-imidazole / dichloromethane / 0.17 h / 0 °C

3.1: sodium hydride / tetrahydrofuran; toluene; mineral oil / 1 h / 20 °C / Cooling with ice

4.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / -10 - 20 °C

4.2: 2 h / 0 - 20 °C

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 5 h / 20 °C / Cooling with ice

6.1: triethylamine / dichloromethane / 3 h / 20 °C

7.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.5 h / -78 °C

8.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C / Cooling with ice

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

10.1: 1H-imidazole; iodine; triphenylphosphine / toluene / 4 h / 60 °C / Reflux

With 1H-imidazole; dmap; sodium tetrahydroborate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; cerium(III) chloride heptahydrate; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; iodine; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; In tetrahydrofuran; methanol; dichloromethane; toluene; mineral oil;
DOI:10.1016/j.tetasy.2011.07.009