(3S,4R,5S,6S)-6-Acetoxy-4-acetylamino-3-tert-butoxycarbonylamino-5-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Base Information

Chemical Name:(3S,4R,5S,6S)-6-Acetoxy-4-acetylamino-3-tert-butoxycarbonylamino-5-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester
CAS No.:208589-22-4
Molecular Formula:C₂₃H₃₈N₂O₈
Molecular Weight:470.563
Hs Code.:

Synonyms:(3S,4R,5S,6S)-6-Acetoxy-4-acetylamino-3-tert-butoxycarbonylamino-5-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

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Chemical Property of (3S,4R,5S,6S)-6-Acetoxy-4-acetylamino-3-tert-butoxycarbonylamino-5-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

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Technology Process of (3S,4R,5S,6S)-6-Acetoxy-4-acetylamino-3-tert-butoxycarbonylamino-5-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

There total 9 articles about (3S,4R,5S,6S)-6-Acetoxy-4-acetylamino-3-tert-butoxycarbonylamino-5-(1-ethyl-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: 96.0%

: 108-24-7
acetic anhydride

: 208589-21-3
(3S,4R,5S,6S)-4-Acetylamino-3-tert-butoxycarbonylamino-5-(1-ethyl-propoxy)-6-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

: 208589-22-4
(3S,4R,5S,6S)-6-Acetoxy-4-acetylamino-3-tert-butoxycarbonylamino-5-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: With pyridine; dmap; for 2.5h; Ambient temperature;
DOI:10.1021/jm980162u

Reference yield:

: 584-02-1
2-pentanol

: 208589-22-4
(3S,4R,5S,6S)-6-Acetoxy-4-acetylamino-3-tert-butoxycarbonylamino-5-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: BF₃*Et₂O / 2 h / 70 - 75 °C

2: pyridine, (dimethylamino)pyridine / 18 h / Ambient temperature

3: Ph₃P, H₂O / tetrahydrofuran / 10 h / 50 °C

4: Et₃N / tetrahydrofuran / 0.67 h / 0 - 20 °C

5: OsO₄, N-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 70 °C

6: 75 percent / SO₂Cl₂, pyridine / CH₂Cl₂ / 0.17 h / -78 °C

7: 1.) 1,8-diazabicyclo<5.4.0>undec-7-ene, 2.) 1N aq. H₂SO₄ / 1.) THF, RT, 16 h, 2.) THF, RT, 40 min

8: 96 percent / pyridine, (dimethylamino)pyridine / 2.5 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; sulfuryl dichloride; sulfuric acid; boron trifluoride diethyl etherate; water; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1021/jm980162u

Reference yield:

: 196618-13-0
oseltamivir

: 208589-22-4
(3S,4R,5S,6S)-6-Acetoxy-4-acetylamino-3-tert-butoxycarbonylamino-5-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 0.67 h / 0 - 20 °C

2: OsO₄, N-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 70 °C

3: 75 percent / SO₂Cl₂, pyridine / CH₂Cl₂ / 0.17 h / -78 °C

4: 1.) 1,8-diazabicyclo<5.4.0>undec-7-ene, 2.) 1N aq. H₂SO₄ / 1.) THF, RT, 16 h, 2.) THF, RT, 40 min

5: 96 percent / pyridine, (dimethylamino)pyridine / 2.5 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; sulfuryl dichloride; sulfuric acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1021/jm980162u