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

Base Information

• Chemical Name: (2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid
• CAS No.: 623936-96-9
• Molecular Formula: C₃₄H₅₅NO₈
• Molecular Weight: 605.813

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

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

Chemical Property:

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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

There total 7 articles about (2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic 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: 98.0%

(2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-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 (623936-96-9)

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-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid (623936-96-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / benzene / 12 h / 80 °C

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

3: D-(-)-DET; Ti(Oi-Pr)4; TBHP / CH₂Cl₂ / 24 h / -20 °C

4: 65 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 0.5 h / 0 °C

5: EDCI; DMAP / CH₂Cl₂ / 2 h / 25 °C

6: HF*Pyr / tetrahydrofuran / 12 h / 25 °C

7: 85 percent / EDCI; DMAP / CH₂Cl₂ / 2 h / 25 °C

8: 98 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 25 °C

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

DOI:10.1016/j.tetlet.2003.08.013

Reference yield:

(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-octadec-2-en-1-ol (623936-80-1) → (2S,3R)-3-[(1S,2R)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-1-methyl-pentadecyl]-oxirane-2-carboxylic acid (623936-96-9)

Guidance literature:

Multi-step reaction with 6 steps

1: D-(-)-DET; Ti(Oi-Pr)4; TBHP / CH₂Cl₂ / 24 h / -20 °C

2: 65 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 0.5 h / 0 °C

3: EDCI; DMAP / CH₂Cl₂ / 2 h / 25 °C

4: HF*Pyr / tetrahydrofuran / 12 h / 25 °C

5: 85 percent / EDCI; DMAP / CH₂Cl₂ / 2 h / 25 °C

6: 98 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 25 °C

With morpholine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethyl (2S,3S)-tartrate; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile; 1: asymmetric Sharpless epoxidation;

DOI:10.1016/j.tetlet.2003.08.013

upstream raw materials:

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

(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-hexadecanal

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

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

Downstream 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

(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

(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)-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

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