(1S,2R,3S,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-(1-ethyl-propoxy)-1,2-dihydroxy-cyclohexanecarboxylic acid ethyl ester

Base Information

Chemical Name:(1S,2R,3S,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-(1-ethyl-propoxy)-1,2-dihydroxy-cyclohexanecarboxylic acid ethyl ester
CAS No.:208589-20-2
Molecular Formula:C₂₁H₃₈N₂O₈
Molecular Weight:446.541
Hs Code.:

Synonyms:(1S,2R,3S,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-(1-ethyl-propoxy)-1,2-dihydroxy-cyclohexanecarboxylic acid ethyl ester

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Chemical Property of (1S,2R,3S,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-(1-ethyl-propoxy)-1,2-dihydroxy-cyclohexanecarboxylic acid ethyl ester

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Technology Process of (1S,2R,3S,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-(1-ethyl-propoxy)-1,2-dihydroxy-cyclohexanecarboxylic acid ethyl ester

There total 6 articles about (1S,2R,3S,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-(1-ethyl-propoxy)-1,2-dihydroxy-cyclohexanecarboxylic 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:

: 367252-68-4
(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

: 208589-20-2
(1S,2R,3S,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-(1-ethyl-propoxy)-1,2-dihydroxy-cyclohexanecarboxylic acid ethyl ester

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; tert-butyl alcohol; at 70 ℃; for 3h; Yield given;
DOI:10.1021/jm980162u

Reference yield:

: 584-02-1
2-pentanol

: 208589-20-2
(1S,2R,3S,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-(1-ethyl-propoxy)-1,2-dihydroxy-cyclohexanecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 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

With pyridine; dmap; osmium(VIII) oxide; boron trifluoride diethyl etherate; water; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1021/jm980162u

Reference yield:

: 196618-13-0
oseltamivir

: 208589-20-2
(1S,2R,3S,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-(1-ethyl-propoxy)-1,2-dihydroxy-cyclohexanecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 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

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1021/jm980162u