(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Base Information

Chemical Name:(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
CAS No.:1443055-47-7
Molecular Formula:C₁₆H₂₇NO₅
Molecular Weight:313.394
Hs Code.:

Synonyms:(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Chemical Property:

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Technology Process of (3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

There total 1 articles about (3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 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: 95.0%

: 75-05-8,26809-02-9
acetonitrile

: 204254-96-6,1217834-81-5,1266663-89-1,2413185-89-2
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

: 1443055-47-7
(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Guidance literature:: acetonitrile; (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester; With boron trifluoride diethyl etherate; at 0 ℃; for 1.16667h;

With water; In acetonitrile; at 0 - 20 ℃; for 4h;

With potassium carbonate; In acetonitrile; at 20 ℃; for 36h; diastereoselective reaction;
DOI:10.1016/j.tetasy.2013.04.016

Reference yield: 98.0%

: 1443055-47-7
(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

: 124-63-0
methanesulfonyl chloride

: 332047-23-1
(3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Guidance literature:: With dmap; triethylamine; at 0 ℃; for 1h;
DOI:10.1016/j.tetasy.2013.04.016

Reference yield:

: 1443055-47-7
(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

: 204255-11-8
oseltamivir phosphate

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine; dmap / 1 h / 0 °C

2.1: sodium hydride / dichloromethane; dimethyl sulfoxide; mineral oil / 8 h / 20 °C

3.1: boron trifluoride diethyl etherate / dichloromethane / 0.37 h / -15 °C

4.1: caesium carbonate / dimethyl sulfoxide / 0.25 h / 80 °C

4.2: 0.33 h / 80 °C

5.1: phosphoric acid / ethyl acetate; ethanol / 2 h / 50 °C

With dmap; phosphoric acid; boron trifluoride diethyl etherate; sodium hydride; caesium carbonate; triethylamine; In ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; mineral oil;
DOI:10.1016/j.tetasy.2013.04.016