(2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid allyl ester

Base Information

Chemical Name:(2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid allyl ester
CAS No.:623937-20-2
Molecular Formula:C₅₃H₈₁N₃O₁₀
Molecular Weight:920.24
Hs Code.:

(2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid allyl ester

Synonyms:(2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid allyl ester

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Chemical Property of (2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid allyl ester

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Technology Process of (2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid allyl ester

There total 4 articles about (2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-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: 81.0%

: (2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyric acid allyl ester

: 623937-18-8
(E)-(4R,5R)-5-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoic acid

: 623937-20-2
(2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid allyl ester

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 25 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2003.08.013

Reference yield:

: 623937-14-4
(E)-(4R,5R)-5-Hydroxy-4-methyl-octadec-2-enoic acid allyl ester

: 623937-20-2
(2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid allyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / EDCI; DMAP / CH₂Cl₂ / 2 h / 25 °C

2: 98 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 25 °C

3: 81 percent / EDCI; HOBt / CH₂Cl₂ / 0.5 h / 25 °C

With morpholine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2003.08.013

Reference yield:

: 623937-12-2
(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-octadec-2-enoic acid allyl ester

: 623937-20-2
(2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid allyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / HF*Pyr / tetrahydrofuran / 12 h / 25 °C

2: 82 percent / EDCI; DMAP / CH₂Cl₂ / 2 h / 25 °C

3: 98 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 25 °C

4: 81 percent / EDCI; HOBt / CH₂Cl₂ / 0.5 h / 25 °C

With morpholine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzotriazol-1-ol; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2003.08.013