(2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid

Base Information

• Chemical Name: (2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid
• CAS No.: 623937-02-0
• Molecular Formula: C₅₀H₇₇N₃O₁₁
• Molecular Weight: 896.175

Synonyms:(2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid

Chemical Property of (2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid

There total 18 articles about (2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid 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: 97.0%

(2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid allyl ester (623937-00-8) → (2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid (623937-02-0)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2003.08.013

Reference yield:

(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-hexadecanal (452956-81-9) → (2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid (623937-02-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 92 percent / benzene / 12 h / Heating

2.1: 98 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 91 percent / Ti(i-PrO)4; (-)-DET; TBHP / CH₂Cl₂; decane / 24 h / -20 °C

4.1: 64 percent / NaIO₄; RuCl₃ / CCl₄; acetonitrile; H₂O / 0.5 h / 0 °C

5.1: 70 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1 h / 25 °C

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

7.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 0 °C

7.2: 86 percent / 4-dimethylaminopyridine / tetrahydrofuran; toluene / 0 - 25 °C

8.1: 94 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 25 °C

With morpholine; titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium trichloride; sodium periodate; 2,4,6-trichlorobenzoyl chloride; diisobutylaluminium hydride; pyridine hydrogenfluoride; (-)-diethyl tartrate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; tetrachloromethane; decane; dichloromethane; water; acetonitrile; benzene; 3.1: Sharpless asymmetric epoxidation;

DOI:10.1021/jo050625l

Reference yield:

(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-octadec-2-en-1-ol (623936-80-1) → (2S,3R)-3-Benzyloxy-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-butyric acid (623937-02-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 91 percent / Ti(i-PrO)4; (-)-DET; TBHP / CH₂Cl₂; decane / 24 h / -20 °C

2.1: 64 percent / NaIO₄; RuCl₃ / CCl₄; acetonitrile; H₂O / 0.5 h / 0 °C

3.1: 70 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1 h / 25 °C

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

5.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 0 °C

5.2: 86 percent / 4-dimethylaminopyridine / tetrahydrofuran; toluene / 0 - 25 °C

6.1: 94 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 25 °C

With morpholine; titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium trichloride; sodium periodate; 2,4,6-trichlorobenzoyl chloride; pyridine hydrogenfluoride; (-)-diethyl tartrate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; tetrachloromethane; decane; dichloromethane; water; acetonitrile; 1.1: Sharpless asymmetric epoxidation;

DOI:10.1021/jo050625l

upstream raw materials:

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

(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

(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

myristylaldehyde

Downstream raw materials:

(1S,4S,7S,10S,13R,14S,15R)-7-((R)-1-Benzyloxy-ethyl)-10-benzyloxymethyl-4-isopropyl-14-methyl-13-tridecyl-12,16-dioxa-3,6,9-triaza-bicyclo[13.1.0]hexadecane-2,5,8,11-tetraone

(2S,3R)-2-[(S)-2-({(2S,3R)-3-[(1S,2R)-2-((S)-2-Amino-3-benzyloxy-propionyloxy)-1-methyl-pentadecyl]-oxiranecarbonyl}-amino)-3-methyl-butyrylamino]-3-benzyloxy-butyric acid

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