(2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid allyl ester

Base Information

Chemical Name:(2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid allyl ester
CAS No.:623936-94-7
Molecular Formula:C₃₇H₅₉NO₈
Molecular Weight:645.877
Hs Code.:

Synonyms:(2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid allyl ester

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Chemical Property of (2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid allyl ester

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Technology Process of (2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid allyl ester

There total 14 articles about (2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid allyl 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: 85.0%

: 23680-31-1
BOC-O-benzyl-L-serine

: 623936-91-4
(2S,3R)-3-((1S,2R)-2-Hydroxy-1-methyl-pentadecyl)-oxirane-2-carboxylic acid allyl ester

: 623936-94-7
(2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid allyl ester

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 25 ℃; for 2h;
DOI:10.1016/j.tetlet.2003.08.013

Reference yield:

: 452956-81-9
(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-hexadecanal

: 623936-94-7
(2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / benzene / 12 h / Heating

2: 98 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

3: 91 percent / Ti(i-PrO)4; (-)-DET; TBHP / CH₂Cl₂; decane / 24 h / -20 °C

4: 64 percent / NaIO₄; RuCl₃ / CCl₄; acetonitrile; H₂O / 0.5 h / 0 °C

5: 75 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 25 °C

6: 95 percent / HF*pyridine / tetrahydrofuran / 12 h / 25 °C

7: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / CH₂Cl₂ / 0.67 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; ruthenium trichloride; sodium periodate; diisobutylaluminium hydride; pyridine hydrogenfluoride; (-)-diethyl tartrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; tetrachloromethane; decane; dichloromethane; water; acetonitrile; benzene; 3: Sharpless asymmetric epoxidation;
DOI:10.1021/jo050625l

Reference yield:

: 623936-80-1
(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-octadec-2-en-1-ol

: 623936-94-7
(2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / Ti(i-PrO)4; (-)-DET; TBHP / CH₂Cl₂; decane / 24 h / -20 °C

2: 64 percent / NaIO₄; RuCl₃ / CCl₄; acetonitrile; H₂O / 0.5 h / 0 °C

3: 75 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 25 °C

4: 95 percent / HF*pyridine / tetrahydrofuran / 12 h / 25 °C

5: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / CH₂Cl₂ / 0.67 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; ruthenium trichloride; sodium periodate; pyridine hydrogenfluoride; (-)-diethyl tartrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; tetrachloromethane; decane; dichloromethane; water; acetonitrile; 1: Sharpless asymmetric epoxidation;
DOI:10.1021/jo050625l