(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (R)-1-[(S)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

Base Information

• Chemical Name: (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (R)-1-[(S)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester
• CAS No.: 867155-87-1
• Molecular Formula: C₄₂H₆₅NO₇
• Molecular Weight: 695.981

Synonyms:(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (R)-1-[(S)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

Chemical Property of (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (R)-1-[(S)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (R)-1-[(S)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

There total 4 articles about (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (R)-1-[(S)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl 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: 70.0%

(2S,3R)-2-((4S,5S)-5-Ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-hexadecan-3-ol (867155-84-8) + (R)-N-benzyloxycarbonyl-O-benzyl serine (20806-42-2) → (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (R)-1-[(S)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester (867155-87-1)

Guidance literature:

(R)-N-benzyloxycarbonyl-O-benzyl serine; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 0 ℃; for 1.5h;

(2S,3R)-2-((4S,5S)-5-Ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-hexadecan-3-ol; With dmap; In tetrahydrofuran; toluene; at 0 - 25 ℃;

DOI:10.1021/jo050628y

Reference yield:

(2S,3S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethyl-4-methyl-octadecane-1,3-diol (867155-80-4) → (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (R)-1-[(S)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester (867155-87-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / CSA / dimethylformamide / 0.5 h / 25 °C

2.1: 280 mg / TBAF / tetrahydrofuran / 96 h / 25 °C

3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1.5 h / 0 °C

3.2: 70 percent / 4-DMAP / tetrahydrofuran; toluene / 0 - 25 °C

With 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo050628y

Reference yield:

tert-Butyl-{(R)-1-[(R)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyloxy}-dimethyl-silane (867155-82-6) → (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (R)-1-[(S)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester (867155-87-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 280 mg / TBAF / tetrahydrofuran / 96 h / 25 °C

2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1.5 h / 0 °C

2.2: 70 percent / 4-DMAP / tetrahydrofuran; toluene / 0 - 25 °C

With 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo050628y

upstream raw materials:

(2S,3R)-2-((4S,5S)-5-Ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-hexadecan-3-ol

(R)-N-benzyloxycarbonyl-O-benzyl serine

(2S,3S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethyl-4-methyl-octadecane-1,3-diol

tert-Butyl-{(R)-1-[(R)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyloxy}-dimethyl-silane

Downstream raw materials:

(2R,3R,4R,5R)-5-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-2-ethyl-3-hydroxy-4-methyl-octadecanoic acid

(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionic acid (R)-1-((1R,2S,3S)-2-hydroxy-3-hydroxymethyl-1-methyl-pentyl)-tetradecyl ester

(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionic acid (R)-1-[(S)-1-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionic acid (R)-1-((1R,2R,3R)-3-formyl-2-hydroxy-1-methyl-pentyl)-tetradecyl ester

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