(3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester

Base Information

Chemical Name:(3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester
CAS No.:367252-67-3
Molecular Formula:C₁₉H₃₂N₄O₅
Molecular Weight:396.487
Hs Code.:

Synonyms:(3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester

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Chemical Property of (3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester

Chemical Property:

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MSDS Files:: SDS file from LookChem

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Technology Process of (3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester

There total 9 articles about (3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl 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: 78.0%

: 367252-66-2
(3R,4S,5S)-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-4-trifluoromethanesulfonyloxycyclohex-1-enecarboxylic acid ethyl ester

: 367252-67-3
(3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: With sodium azide; In water; acetone; at 20 ℃; for 15h;
DOI:10.1021/jo800264d

Reference yield:

: 367252-66-2
(3R,4S,5S)-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-4-trifluoromethanesulfonyloxycyclohex-1-enecarboxylic acid ethyl ester

: 67-64-1
acetone

: 367252-67-3
(3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: In hexane; ethyl acetate;

Reference yield:

: 1234286-95-3
ethyl 3,4-O-isopentylidene-5-oxo shikimate

: 367252-67-3
(3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridine; hydroxylamine hydrochloride / ethanol / 2 h / 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate; molybdenum(VI) oxide / methanol / 0.5 h / 20 °C / Inert atmosphere

3.1: triethylsilane; titanium tetrachloride / dichloromethane / 7 h / -78 - -10 °C / Inert atmosphere

3.2: -10 °C / Inert atmosphere

4.1: methanol / 3 h / 20 °C / Inert atmosphere

5.1: pyridine / dichloromethane / 0.5 h / -10 - 0 °C / Inert atmosphere

6.1: sodium azide / water; acetone / 15 h / 20 °C

With pyridine; triethylsilane; sodium tetrahydroborate; sodium azide; hydroxylamine hydrochloride; titanium tetrachloride; molybdenum(VI) oxide; In methanol; ethanol; dichloromethane; water; acetone;
DOI:10.1016/j.tet.2012.06.065