2S-tert-butoxycarbonylamino-4-[(2S,3R)-2,3,5-tris(p-methoxybenzoyloxy)-4-oxo-pentane-1-mercaptan]-butyric acid tert-butyl ester

Base Information

Chemical Name:2S-tert-butoxycarbonylamino-4-[(2S,3R)-2,3,5-tris(p-methoxybenzoyloxy)-4-oxo-pentane-1-mercaptan]-butyric acid tert-butyl ester
CAS No.:630108-98-4
Molecular Formula:C₄₂H₅₇NO₁₁S
Molecular Weight:783.981
Hs Code.:

Synonyms:2S-tert-butoxycarbonylamino-4-[(2S,3R)-2,3,5-tris(p-methoxybenzoyloxy)-4-oxo-pentane-1-mercaptan]-butyric acid tert-butyl ester

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Chemical Property of 2S-tert-butoxycarbonylamino-4-[(2S,3R)-2,3,5-tris(p-methoxybenzoyloxy)-4-oxo-pentane-1-mercaptan]-butyric acid tert-butyl ester

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Technology Process of 2S-tert-butoxycarbonylamino-4-[(2S,3R)-2,3,5-tris(p-methoxybenzoyloxy)-4-oxo-pentane-1-mercaptan]-butyric acid tert-butyl ester

There total 9 articles about 2S-tert-butoxycarbonylamino-4-[(2S,3R)-2,3,5-tris(p-methoxybenzoyloxy)-4-oxo-pentane-1-mercaptan]-butyric acid tert-butyl 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:

: 630108-94-0
N-tert-butoxycarbonyl-L-homocysteine tert-butyl ester

: 630108-95-1
(4R,5R,6R)-2,6-bis(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)-[1,3,2]dioxathiepane 2,2-dioxide

: (S)-4-[(1S,2R,3S)-2,3-Bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-4-oxo-butylsulfanyl]-2-tert-butoxycarbonylamino-butyric acid tert-butyl ester

: 630108-98-4
2S-tert-butoxycarbonylamino-4-[(2S,3R)-2,3,5-tris(p-methoxybenzoyloxy)-4-oxo-pentane-1-mercaptan]-butyric acid tert-butyl ester

Guidance literature:: N-tert-butoxycarbonyl-L-homocysteine tert-butyl ester; With n-butyllithium; In hexane; N,N-dimethyl-formamide; for 0.0833333h;

(4R,5R,6R)-2,6-bis(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)-[1,3,2]dioxathiepane 2,2-dioxide; In hexane; N,N-dimethyl-formamide; for 2h;

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ja0369663

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 630108-98-4
2S-tert-butoxycarbonylamino-4-[(2S,3R)-2,3,5-tris(p-methoxybenzoyloxy)-4-oxo-pentane-1-mercaptan]-butyric acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: aq. Na₂CO₃ / dioxane / 20 °C

2.1: N,N'-diisopropylcarbodiimide; CuCl / CH₂Cl₂

2.2: 0.43 g / CH₂Cl₂ / 96 h / Heating

3.1: 100 percent / tributylphosphine / dimethylformamide

4.1: n-BuLi / dimethylformamide; hexane / 0.08 h

4.2: dimethylformamide; hexane / 2 h

4.3: 38 mg / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

With n-butyllithium; tributylphosphine; sodium carbonate; copper(l) chloride; diisopropyl-carbodiimide; In 1,4-dioxane; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0369663

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-lyxose

: 630108-98-4
2S-tert-butoxycarbonylamino-4-[(2S,3R)-2,3,5-tris(p-methoxybenzoyloxy)-4-oxo-pentane-1-mercaptan]-butyric acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: H₂SO₄ / 20 °C

2.1: 2.90 g / aq. KOH; tetrabutylammonium bromide / tetrahydrofuran / 6 h / 90 °C

3.1: DIBAL; di[1,3-bis(diphenylphosphino)propane]dichloronickel(II) / diethyl ether; tetrahydrofuran / 2 h

3.2: 73 percent / NaBH₄ / ethanol / 0.5 h

4.1: Et₃N; SOCl₂ / CH₂Cl₂ / 2.5 h / 0 °C

5.1: 138 mg / RuCl₃; NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / 0 °C

6.1: n-BuLi / dimethylformamide; hexane / 0.08 h

6.2: dimethylformamide; hexane / 2 h

6.3: 38 mg / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

With ruthenium trichloride; potassium hydroxide; sodium periodate; n-butyllithium; thionyl chloride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); sulfuric acid; tetrabutylammomium bromide; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0369663