(3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-carboxymethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Base Information

Chemical Name:(3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-carboxymethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester
CAS No.:252191-17-6
Molecular Formula:C₁₆H₂₆N₂O₆
Molecular Weight:342.392
Hs Code.:

Synonyms:(3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-carboxymethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

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Chemical Property of (3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-carboxymethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

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Technology Process of (3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-carboxymethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

There total 10 articles about (3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-carboxymethyl-propoxy)-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: 86.0%

: (3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-benzhydryloxycarbonylmethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

: 252191-17-6
(3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-carboxymethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: With methoxybenzene; trifluoroacetic acid; In dichloromethane;
DOI:10.1016/S0960-894X(99)00479-5

Reference yield:

: 51795-28-9
(+)-(R)-5-hexen-3-ol

: 252191-17-6
(3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-carboxymethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: BF₃*Et₂O / 75 °C

2: pyridine

3: 78 percent / MCPBA / CH₂Cl₂ / 20 °C

4: 91 percent / aq. HClO₄ / tetrahydrofuran

5: 97 percent / NaIO₄/silica gel

6: CrO₃; H₂SO₄

7: acetone

8: 93 percent / PPh₃ / tetrahydrofuran; H₂O

9: 86 percent / TFA; anisole / CH₂Cl₂

With pyridine; chromium(VI) oxide; sodium periodate; perchloric acid; sulfuric acid; boron trifluoride diethyl etherate; silica gel; methoxybenzene; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone; 1: Ring cleavage / 2: Acetylation / 3: Epoxidation / 4: Ring cleavage / 5: Oxidation / 6: Oxidation / 7: Esterification / 8: Reduction / 9: deprotection;
DOI:10.1016/S0960-894X(99)00479-5

Reference yield:

: (1S,5S,6S)-5-Azido-7-trityl-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid ethyl ester

: 252191-17-6
(3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-carboxymethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: BF₃*Et₂O / 75 °C

2: pyridine

3: 78 percent / MCPBA / CH₂Cl₂ / 20 °C

4: 91 percent / aq. HClO₄ / tetrahydrofuran

5: 97 percent / NaIO₄/silica gel

6: CrO₃; H₂SO₄

7: acetone

8: 93 percent / PPh₃ / tetrahydrofuran; H₂O

9: 86 percent / TFA; anisole / CH₂Cl₂

With pyridine; chromium(VI) oxide; sodium periodate; perchloric acid; sulfuric acid; boron trifluoride diethyl etherate; silica gel; methoxybenzene; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone; 1: Ring cleavage / 2: Acetylation / 3: Epoxidation / 4: Ring cleavage / 5: Oxidation / 6: Oxidation / 7: Esterification / 8: Reduction / 9: deprotection;
DOI:10.1016/S0960-894X(99)00479-5