(2S,3R)-3-Benzyloxy-2-((S)-2-{[(2S,3R)-3-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-oxiranecarbonyl]-amino}-3-methyl-butyrylamino)-butyric acid allyl ester

Base Information

Chemical Name:(2S,3R)-3-Benzyloxy-2-((S)-2-{[(2S,3R)-3-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-oxiranecarbonyl]-amino}-3-methyl-butyrylamino)-butyric acid allyl ester
CAS No.:867038-91-3
Molecular Formula:C₃₈H₆₂N₂O₇
Molecular Weight:658.919
Hs Code.:

Synonyms:(2S,3R)-3-Benzyloxy-2-((S)-2-{[(2S,3R)-3-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-oxiranecarbonyl]-amino}-3-methyl-butyrylamino)-butyric acid allyl ester

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Chemical Property of (2S,3R)-3-Benzyloxy-2-((S)-2-{[(2S,3R)-3-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-oxiranecarbonyl]-amino}-3-methyl-butyrylamino)-butyric acid allyl ester

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Technology Process of (2S,3R)-3-Benzyloxy-2-((S)-2-{[(2S,3R)-3-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-oxiranecarbonyl]-amino}-3-methyl-butyrylamino)-butyric acid allyl ester

There total 12 articles about (2S,3R)-3-Benzyloxy-2-((S)-2-{[(2S,3R)-3-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-oxiranecarbonyl]-amino}-3-methyl-butyrylamino)-butyric 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:

: 867038-90-2
(2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid allyl ester

: 867038-91-3
(2S,3R)-3-Benzyloxy-2-((S)-2-{[(2S,3R)-3-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-oxiranecarbonyl]-amino}-3-methyl-butyrylamino)-butyric acid allyl ester

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 25 ℃; for 12h;
DOI:10.1021/jo050625l

Reference yield:

: {3-[(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-pentadecyl]-oxiranyl}-methanol

: 867038-91-3
(2S,3R)-3-Benzyloxy-2-((S)-2-{[(2S,3R)-3-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-oxiranecarbonyl]-amino}-3-methyl-butyrylamino)-butyric acid allyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 64 percent / NaIO₄; RuCl₃ / CCl₄; acetonitrile; H₂O / 0.5 h / 0 °C

2: 70 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1 h / 25 °C

3: HF*pyridine / tetrahydrofuran / 12 h / 25 °C

With ruthenium trichloride; sodium periodate; pyridine hydrogenfluoride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo050625l

Reference yield:

: 124-25-4,511542-15-7
myristylaldehyde

: 867038-91-3
(2S,3R)-3-Benzyloxy-2-((S)-2-{[(2S,3R)-3-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-oxiranecarbonyl]-amino}-3-methyl-butyrylamino)-butyric acid allyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: (n-Bu)2BOTf; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 85 percent / CH₂Cl₂ / 12 h / -78 °C

2.1: 92 percent / LiBH₄ / tetrahydrofuran / -20 - 0 °C

3.1: 94 percent / pyridine / CH₂Cl₂ / 0.67 h / -20 °C

4.1: 96 percent / imidazole / dimethylformamide / 12 h / 25 °C

5.1: 98 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

7.1: 92 percent / benzene / 12 h / Heating

8.1: 98 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

9.1: 91 percent / Ti(i-PrO)4; (-)-DET; TBHP / CH₂Cl₂; decane / 24 h / -20 °C

10.1: 64 percent / NaIO₄; RuCl₃ / CCl₄; acetonitrile; H₂O / 0.5 h / 0 °C

11.1: 70 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1 h / 25 °C

12.1: HF*pyridine / tetrahydrofuran / 12 h / 25 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium trichloride; sodium periodate; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; (-)-diethyl tartrate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; tetrachloromethane; decane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 6.1: Swern oxidation / 9.1: Sharpless asymmetric epoxidation;
DOI:10.1021/jo050625l