(5S,6S)-6-Acetylamino-5-azido-1-(2-ethyl-butyryl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester

Base Information

Chemical Name:(5S,6S)-6-Acetylamino-5-azido-1-(2-ethyl-butyryl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester
CAS No.:315700-27-7
Molecular Formula:C₂₇H₃₁N₅O₄
Molecular Weight:489.574
Hs Code.:

Synonyms:(5S,6S)-6-Acetylamino-5-azido-1-(2-ethyl-butyryl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester

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Chemical Property of (5S,6S)-6-Acetylamino-5-azido-1-(2-ethyl-butyryl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester

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Technology Process of (5S,6S)-6-Acetylamino-5-azido-1-(2-ethyl-butyryl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester

There total 8 articles about (5S,6S)-6-Acetylamino-5-azido-1-(2-ethyl-butyryl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl 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: 70.0%

: 315700-26-6
(5R,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-5-hydroxy-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester

: 315700-27-7
(5S,6S)-6-Acetylamino-5-azido-1-(2-ethyl-butyryl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester

Guidance literature:: With hydrogen azide; triphenylphosphine; diethylazodicarboxylate; In benzene; at 20 ℃;
DOI:10.1021/ol000261d

Reference yield:

: 908093-98-1
diazodiphenylmethane

: 315700-27-7
(5S,6S)-6-Acetylamino-5-azido-1-(2-ethyl-butyryl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 4 steps

1: methanol / 20 °C

2: Dess-Martin periodane / dichloromethane / 20 °C

3: sodium tetrahydroborate / methanol / -10 - 10 °C

4: hydrogen azide; triphenylphosphine; diethylazodicarboxylate / benzene / 20 °C

With sodium tetrahydroborate; hydrogen azide; Dess-Martin periodane; triphenylphosphine; diethylazodicarboxylate; In methanol; dichloromethane; benzene; 1: Alkylation / 2: Dess-Martin oxidation / 3: Reduction / 4: Mitsunobu reaction;
DOI:10.1021/ol000261d

Reference yield:

: siastatin B methyl ester

: 315700-27-7
(5S,6S)-6-Acetylamino-5-azido-1-(2-ethyl-butyryl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 20 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene

3: sodium hydroxide / methanol; water / 20 °C

4: methanol / 20 °C

5: Dess-Martin periodane / dichloromethane / 20 °C

6: sodium tetrahydroborate / methanol / -10 - 10 °C

7: hydrogen azide; triphenylphosphine; diethylazodicarboxylate / benzene / 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; hydrogen azide; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; diethylazodicarboxylate; In methanol; dichloromethane; water; benzene; 1: Acylation / 2: Dehydration / 3: Hydrolysis / 4: Alkylation / 5: Dess-Martin oxidation / 6: Reduction / 7: Mitsunobu reaction;
DOI:10.1021/ol000261d