(3S,4Z,6S,7S,8S,9Z,12S,13R,14S,15S,16S)-15-(carbamoyloxy)-3,7,13-trihydroxy-6,8,10,12,14,16-hexamethylicosa-4,9-dienyl 3-(dimethylamino)benzoate

Base Information

Chemical Name:(3S,4Z,6S,7S,8S,9Z,12S,13R,14S,15S,16S)-15-(carbamoyloxy)-3,7,13-trihydroxy-6,8,10,12,14,16-hexamethylicosa-4,9-dienyl 3-(dimethylamino)benzoate
CAS No.:1334327-35-3
Molecular Formula:C₃₆H₆₀N₂O₇
Molecular Weight:632.882
Hs Code.:

Synonyms:(3S,4Z,6S,7S,8S,9Z,12S,13R,14S,15S,16S)-15-(carbamoyloxy)-3,7,13-trihydroxy-6,8,10,12,14,16-hexamethylicosa-4,9-dienyl 3-(dimethylamino)benzoate

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Chemical Property of (3S,4Z,6S,7S,8S,9Z,12S,13R,14S,15S,16S)-15-(carbamoyloxy)-3,7,13-trihydroxy-6,8,10,12,14,16-hexamethylicosa-4,9-dienyl 3-(dimethylamino)benzoate

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Technology Process of (3S,4Z,6S,7S,8S,9Z,12S,13R,14S,15S,16S)-15-(carbamoyloxy)-3,7,13-trihydroxy-6,8,10,12,14,16-hexamethylicosa-4,9-dienyl 3-(dimethylamino)benzoate

There total 10 articles about (3S,4Z,6S,7S,8S,9Z,12S,13R,14S,15S,16S)-15-(carbamoyloxy)-3,7,13-trihydroxy-6,8,10,12,14,16-hexamethylicosa-4,9-dienyl 3-(dimethylamino)benzoate 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: 18.0%

: 1334327-44-4
C₂₇H₅₁NO₆

: 99-64-9
3-(dimethylamino)benzoic acid

: 1334327-35-3
(3S,4Z,6S,7S,8S,9Z,12S,13R,14S,15S,16S)-15-(carbamoyloxy)-3,7,13-trihydroxy-6,8,10,12,14,16-hexamethylicosa-4,9-dienyl 3-(dimethylamino)benzoate

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1016/j.bmc.2011.06.082

Reference yield:

: 870074-98-9
tert-Butyl-[(1S,2R,3S,4S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octyloxy]-dimethyl-silane

: 1334327-35-3
(3S,4Z,6S,7S,8S,9Z,12S,13R,14S,15S,16S)-15-(carbamoyloxy)-3,7,13-trihydroxy-6,8,10,12,14,16-hexamethylicosa-4,9-dienyl 3-(dimethylamino)benzoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: tert.-butyl lithium; 9-methoxy-9-BBN / tetrahydrofuran; diethyl ether; hexane; pentane / 1 h / -78 - 20 °C / Inert atmosphere

1.2: 20 h / 20 °C / Inert atmosphere; Darkness

2.1: hydrogenchloride / ethanol / 0.33 h / 20 °C / Inert atmosphere

3.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: 18-crown-6 ether; potassium carbonate / N,N,N,N,N,N-hexamethylphosphoric triamide; toluene / 18 h / -10 - -5 °C / Inert atmosphere

5.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / pH 7 / aq. buffer

6.1: dichloromethane / 1.5 h / 20 °C / Inert atmosphere

6.2: 2 h / 20 °C / Inert atmosphere

7.1: potassium tri-sec-butyl-borohydride / tetrahydrofuran; toluene / 2 h / -78 °C / Inert atmosphere

7.2: -78 °C / Inert atmosphere

8.1: hydrogenchloride; water / methanol / 4 h / 20 °C

9.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; 18-crown-6 ether; water; tert.-butyl lithium; sulfur trioxide pyridine complex; potassium tri-sec-butyl-borohydride; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 9-methoxy-9-BBN; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; toluene; pentane; 1.2: Suzuki coupling / 3.1: Parikh-Doering oxidation / 4.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2011.06.082

Reference yield:

: 1334327-40-0
(8Z,10S,11S,12S,13Z,16S,17R)-17-((2R,3S,4S)-3-(4-methoxybenzyloxy)-4-methyloctan-2-yl)-11-(methoxymethyloxy)-2,2,3,3,10,12,14,16,19,19,20,20-dodecamethyl-4,18-dioxa-3,19-disilahenicosa-8,13-dien-7-one

: 1334327-35-3
(3S,4Z,6S,7S,8S,9Z,12S,13R,14S,15S,16S)-15-(carbamoyloxy)-3,7,13-trihydroxy-6,8,10,12,14,16-hexamethylicosa-4,9-dienyl 3-(dimethylamino)benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / pH 7 / aq. buffer

2.1: dichloromethane / 1.5 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: potassium tri-sec-butyl-borohydride / tetrahydrofuran; toluene / 2 h / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: hydrogenchloride; water / methanol / 4 h / 20 °C

5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; water; potassium tri-sec-butyl-borohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1016/j.bmc.2011.06.082