(R)-5-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionylamino]-2-methoxycarbonyl-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Chemical Name:(R)-5-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionylamino]-2-methoxycarbonyl-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
CAS No.:861099-91-4
Molecular Formula:C₃₄H₄₆IN₃O₉
Molecular Weight:767.658
Hs Code.:

(R)-5-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionylamino]-2-methoxycarbonyl-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Synonyms:(R)-5-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionylamino]-2-methoxycarbonyl-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Chemical Property of (R)-5-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionylamino]-2-methoxycarbonyl-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Technology Process of (R)-5-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionylamino]-2-methoxycarbonyl-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

There total 8 articles about (R)-5-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionylamino]-2-methoxycarbonyl-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl 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: 81.0%

: 861099-81-2
2-tert-butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionic acid

: (R)-5-((R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

: 861099-91-4
(R)-5-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionylamino]-2-methoxycarbonyl-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃;
DOI:10.1021/ol050949w

Reference yield:

: 2-isopropyloxy-5-iodo-benzyl bromide

: 861099-91-4
(R)-5-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionylamino]-2-methoxycarbonyl-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / CsOH; O-⁽⁹⁾-allyl-N-(9'-anthracenylmethyl)cinchonidinium bromide / CH₂Cl₂; H₂O / -50 °C

2: 61 percent / aq. citric acid / tetrahydrofuran / 20 °C

3: 100 percent / aq. HCl / CHCl₃ / 20 °C

4: 77 percent / AcBr / 0 °C

5: 95 percent / K₂CO₃ / dioxane; H₂O

6: 99 percent / aq. LiOH / dioxane

7: 81 percent / EDC; HOBt / CH₂Cl₂ / 20 °C

With hydrogenchloride; cesium hydroxide; lithium hydroxide; Acetyl bromide; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; citric acid; (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water;
DOI:10.1021/ol050949w

Reference yield:

: (5S)-N-benzyloxycarbonyl-5-bromomethyloxazolidine

: 861099-91-4
(R)-5-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(5-iodo-2-isopropoxy-phenyl)-propionylamino]-2-methoxycarbonyl-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 42 percent / BuLi / tetrahydrofuran / 0.5 h / -78 °C

2: 81 percent / EDC; HOBt / CH₂Cl₂ / 20 °C

With n-butyllithium; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol050949w