5-[(Z)-(R)-2-Allyloxycarbonylamino-8-(toluene-4-sulfonyloxy)-oct-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

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Chemical Name:5-[(Z)-(R)-2-Allyloxycarbonylamino-8-(toluene-4-sulfonyloxy)-oct-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
CAS No.:211511-73-8
Molecular Formula:C₂₉H₄₂N₂O₇S
Molecular Weight:562.728
Hs Code.:

Synonyms:5-[(Z)-(R)-2-Allyloxycarbonylamino-8-(toluene-4-sulfonyloxy)-oct-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

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Chemical Property of 5-[(Z)-(R)-2-Allyloxycarbonylamino-8-(toluene-4-sulfonyloxy)-oct-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

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Technology Process of 5-[(Z)-(R)-2-Allyloxycarbonylamino-8-(toluene-4-sulfonyloxy)-oct-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

There total 12 articles about 5-[(Z)-(R)-2-Allyloxycarbonylamino-8-(toluene-4-sulfonyloxy)-oct-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl 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: 88.0%

: 98-59-9
p-toluenesulfonyl chloride

: 211511-82-9
5-((Z)-(R)-2-Allyloxycarbonylamino-8-hydroxy-oct-3-enyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

: 211511-73-8
5-[(Z)-(R)-2-Allyloxycarbonylamino-8-(toluene-4-sulfonyloxy)-oct-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; 1.) 0 deg C, 30 min, 2.) room temp., overnight;
DOI:10.1016/S0040-4020(98)00346-9

Reference yield:

: 100-55-0
3-hydroxymethylpyridin

: 211511-73-8
5-[(Z)-(R)-2-Allyloxycarbonylamino-8-(toluene-4-sulfonyloxy)-oct-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: CH₂Cl₂ / Ambient temperature

2: 530 g / NaBH₄ / methanol / 8 h / Ambient temperature

3: 60 percent / NaHCO₃ / benzene / 1.) room temp., 2 h, 2.) reflux, 16 h

4: 1.) aq. KOH, 2.) NaHCO₃ / 1.) MeOH, reflux, 18 h, 2.) MeOH, H₂O, 0 deg C, 1 h, then room temp., 4 h

5: 93 percent / Br₂, Ph₃P, imidazole / CH₂Cl₂ / 18 h / Ambient temperature

6: 1.) diisopropylamin, BuLi, LiCl / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, 0 deg C, 1 h

7: dioxane / 1.) 0 deg C, 30 min, 2.) room temp., 1 h

8: 93 percent / aq. NaOH / methanol / 3 h / Heating

9: 1.) N-methyl-morpholine, isobutyl chloroformate / 1.) CH₂Cl₂, -30 deg C, 3 h, 2.) CH₂Cl₂, room temp., 8 h

10: 83 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

11: 1.) KHMDS / 1.) THF, toluene, 0 deg C, 1.5 h, 2.) THF, toluene, -78 deg C, 45 min, room temp., 2 h

12: 99 percent / PPTS / methanol / 3 h / Ambient temperature

13: 88 percent / Et₃N, DMAP / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temp., overnight

With 4-methyl-morpholine; 1H-imidazole; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; bromine; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydrogencarbonate; triethylamine; diisopropylamine; triphenylphosphine; lithium chloride; isobutyl chloroformate; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4020(98)00346-9

Reference yield:

: 244267-39-8
(1-Benzyl-1,2,5,6,tetrahydro-pyridin-3-yl)-methanol

: 211511-73-8
5-[(Z)-(R)-2-Allyloxycarbonylamino-8-(toluene-4-sulfonyloxy)-oct-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 60 percent / NaHCO₃ / benzene / 1.) room temp., 2 h, 2.) reflux, 16 h

2: 1.) aq. KOH, 2.) NaHCO₃ / 1.) MeOH, reflux, 18 h, 2.) MeOH, H₂O, 0 deg C, 1 h, then room temp., 4 h

3: 93 percent / Br₂, Ph₃P, imidazole / CH₂Cl₂ / 18 h / Ambient temperature

4: 1.) diisopropylamin, BuLi, LiCl / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, 0 deg C, 1 h

5: dioxane / 1.) 0 deg C, 30 min, 2.) room temp., 1 h

6: 93 percent / aq. NaOH / methanol / 3 h / Heating

7: 1.) N-methyl-morpholine, isobutyl chloroformate / 1.) CH₂Cl₂, -30 deg C, 3 h, 2.) CH₂Cl₂, room temp., 8 h

8: 83 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

9: 1.) KHMDS / 1.) THF, toluene, 0 deg C, 1.5 h, 2.) THF, toluene, -78 deg C, 45 min, room temp., 2 h

10: 99 percent / PPTS / methanol / 3 h / Ambient temperature

11: 88 percent / Et₃N, DMAP / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temp., overnight

With 4-methyl-morpholine; 1H-imidazole; dmap; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; bromine; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydrogencarbonate; triethylamine; diisopropylamine; triphenylphosphine; lithium chloride; isobutyl chloroformate; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4020(98)00346-9