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

Base Information

• Chemical Name: (S)-2-[((2S,3R)-3-{(1S,2R)-2-[(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-propionyloxy]-1-methyl-pentadecyl}-oxiranecarbonyl)-amino]-3-methyl-butyric acid
• CAS No.: 867038-98-0
• Molecular Formula: C₅₀H₇₇N₃O₁₁
• Molecular Weight: 896.175
• Mol file: 867038-98-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (S)-2-[((2S,3R)-3-{(1S,2R)-2-[(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-propionyloxy]-1-methyl-pentadecyl}-oxiranecarbonyl)-amino]-3-methyl-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: 95.0%

(S)-2-[((2S,3R)-3-{(1S,2R)-2-[(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-propionyloxy]-1-methyl-pentadecyl}-oxiranecarbonyl)-amino]-3-methyl-butyric acid allyl ester (867038-97-9) → (S)-2-[((2S,3R)-3-{(1S,2R)-2-[(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-propionyloxy]-1-methyl-pentadecyl}-oxiranecarbonyl)-amino]-3-methyl-butyric acid (867038-98-0)

Guidance literature:

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

DOI:10.1021/jo050625l

Reference yield:

(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-hexadecanal (452956-81-9) → (S)-2-[((2S,3R)-3-{(1S,2R)-2-[(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-propionyloxy]-1-methyl-pentadecyl}-oxiranecarbonyl)-amino]-3-methyl-butyric acid (867038-98-0)

Guidance literature:

Multi-step reaction with 10 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: EDCI; DMAP / CH₂Cl₂ / 25 °C

8: Pd(PPh₃)4; morpholine / tetrahydrofuran / 25 °C

9: EDCI; HOBt / CH₂Cl₂ / 25 °C

10: Pd(PPh₃)4; morpholine / tetrahydrofuran / 25 °C

With morpholine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; benzotriazol-1-ol; 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) → (S)-2-[((2S,3R)-3-{(1S,2R)-2-[(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)-propionyloxy]-1-methyl-pentadecyl}-oxiranecarbonyl)-amino]-3-methyl-butyric acid (867038-98-0)

Guidance literature:

Multi-step reaction with 8 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: EDCI; DMAP / CH₂Cl₂ / 25 °C

6: Pd(PPh₃)4; morpholine / tetrahydrofuran / 25 °C

7: EDCI; HOBt / CH₂Cl₂ / 25 °C

8: Pd(PPh₃)4; morpholine / tetrahydrofuran / 25 °C

With morpholine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethyl (2S,3S)-tartrate; benzotriazol-1-ol; 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:

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

L-valine allyl ester

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

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