ethyl (3S,4R,5R)-3-azido-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

Base Information

Chemical Name:ethyl (3S,4R,5R)-3-azido-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate
CAS No.:1388051-86-2
Molecular Formula:C₁₀H₁₅N₃O₆S
Molecular Weight:305.312
Hs Code.:

Synonyms:ethyl (3S,4R,5R)-3-azido-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

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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 ethyl (3S,4R,5R)-3-azido-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

Chemical Property:

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Technology Process of ethyl (3S,4R,5R)-3-azido-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

There total 1 articles about ethyl (3S,4R,5R)-3-azido-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate 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%

: 1388051-82-8
ethyl (3R,4S,5R)-3,4-O-thionyl-5-O-methanesulfonylshikimate

: 1388051-86-2
ethyl (3S,4R,5R)-3-azido-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

Guidance literature:: With sodium azide; ammonium chloride; In water; N,N-dimethyl-formamide; at 20 ℃; for 9h;
DOI:10.1016/j.tetasy.2012.05.014

Reference yield:

: 1388051-86-2
ethyl (3S,4R,5R)-3-azido-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

: 204255-06-1
oseltamivir

Guidance literature:: Multi-step reaction with 6 steps

1.1: triphenylphosphine / ethanol / 0.33 h / 0 °C

1.2: 3 h / 0 - 20 °C

1.3: 3 h / Reflux

2.1: triethylamine / dichloromethane; water / 0.5 h / 0 °C

3.1: boron trifluoride diethyl etherate / 1.5 h / -8 °C

4.1: dmap; triethylamine / ethyl acetate / 1 h / 0 °C

5.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C

6.1: sodium azide; lithium chloride / N,N-dimethyl-formamide / 3 h / 80 °C

With dmap; sodium azide; boron trifluoride diethyl etherate; sodium hydride; triethylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 1.1: Staudinger reduction;
DOI:10.1016/j.tetasy.2012.05.014

Reference yield:

: 1388051-86-2
ethyl (3S,4R,5R)-3-azido-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

: ethyl (3R,4R,5S)-4-acetamido-3-(1-ethylpropoxy)-5-hydroxycyclohex-1-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: triphenylphosphine / ethanol / 0.33 h / 0 °C

1.2: 3 h / 0 - 20 °C

1.3: 3 h / Reflux

2.1: triethylamine / dichloromethane; water / 0.5 h / 0 °C

3.1: boron trifluoride diethyl etherate / 1.5 h / -8 °C

With boron trifluoride diethyl etherate; triethylamine; triphenylphosphine; In ethanol; dichloromethane; water; 1.1: Staudinger reduction;
DOI:10.1016/j.tetasy.2012.05.014