(2S,3S)-2-[(S)-4-Benzyloxycarbonyl-2-((S)-4-benzyloxycarbonyl-2-{(R)-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-2-methylcarbamoylmethyl-propionylamino}-butyrylamino)-butyrylamino]-3-methyl-pentanoic acid benzyl ester

Base Information

• Chemical Name: (2S,3S)-2-[(S)-4-Benzyloxycarbonyl-2-((S)-4-benzyloxycarbonyl-2-{(R)-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-2-methylcarbamoylmethyl-propionylamino}-butyrylamino)-butyrylamino]-3-methyl-pentanoic acid benzyl ester
• CAS No.: 397883-85-1
• Molecular Formula: C₆₃H₇₁N₄O₁₄P
• Molecular Weight: 1139.25

Synonyms:(2S,3S)-2-[(S)-4-Benzyloxycarbonyl-2-((S)-4-benzyloxycarbonyl-2-{(R)-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-2-methylcarbamoylmethyl-propionylamino}-butyrylamino)-butyrylamino]-3-methyl-pentanoic acid benzyl ester

Chemical Property of (2S,3S)-2-[(S)-4-Benzyloxycarbonyl-2-((S)-4-benzyloxycarbonyl-2-{(R)-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-2-methylcarbamoylmethyl-propionylamino}-butyrylamino)-butyrylamino]-3-methyl-pentanoic acid benzyl ester

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Technology Process of (2S,3S)-2-[(S)-4-Benzyloxycarbonyl-2-((S)-4-benzyloxycarbonyl-2-{(R)-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-2-methylcarbamoylmethyl-propionylamino}-butyrylamino)-butyrylamino]-3-methyl-pentanoic acid benzyl ester

There total 15 articles about (2S,3S)-2-[(S)-4-Benzyloxycarbonyl-2-((S)-4-benzyloxycarbonyl-2-{(R)-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-2-methylcarbamoylmethyl-propionylamino}-butyrylamino)-butyrylamino]-3-methyl-pentanoic acid benzyl 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: 67.0%

(2S,3S)-2-[(S)-2-((S)-2-Amino-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester; hydrochloride + (2R)-2-[4-(bis-benzyloxy-phosphoryloxy)-benzyl]-N-methyl-succinamic acid (397883-83-9) → (2S,3S)-2-[(S)-4-Benzyloxycarbonyl-2-((S)-4-benzyloxycarbonyl-2-{(R)-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-2-methylcarbamoylmethyl-propionylamino}-butyrylamino)-butyrylamino]-3-methyl-pentanoic acid benzyl ester (397883-85-1)

Guidance literature:

(2R)-2-[4-(bis-benzyloxy-phosphoryloxy)-benzyl]-N-methyl-succinamic acid; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 0.5h;

(2S,3S)-2-[(S)-2-((S)-2-Amino-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester; hydrochloride; With 4-methyl-morpholine; In tetrahydrofuran; at 0 - 20 ℃; Further stages.;

DOI:10.1021/ja011746f

Reference yield:

4-tert-butoxybromobenzene (60876-70-2) → (2S,3S)-2-[(S)-4-Benzyloxycarbonyl-2-((S)-4-benzyloxycarbonyl-2-{(R)-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-2-methylcarbamoylmethyl-propionylamino}-butyrylamino)-butyrylamino]-3-methyl-pentanoic acid benzyl ester (397883-85-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Na₂CO₃; PdCl₂ / H₂O / 24 h / Heating

1.2: 92 percent / Pd/C / 8 h / 20 °C / 760.05 Torr

2.1: Et₃N; trimethylacetyl chloride / tetrahydrofuran / 2 h / -15 °C

2.2: 82 percent / lithium chloride / 20 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 71 percent / tetrahydrofuran

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

4.2: 91 percent / tetrahydrofuran / 2 h / -78 - -10 °C

5.1: 98 percent / trifluoroacetic acid / 0.5 h

6.1: 100 percent / Pd/C / ethanol / 0.5 h / 760.05 Torr

7.1: N-methylmorpholine; tert-butyldimethylsilyl chloride / tetrahydrofuran / 1 h / 20 °C

7.2: 1-H-tetrazole / tetrahydrofuran / 20 °C

7.3: 72 percent / tert-butyl hydroperoxide / tetrahydrofuran / -10 - 20 °C

8.1: hydroxybenzotriazole; dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 0 °C

8.2: 67 percent / NMM / tetrahydrofuran / 0 - 20 °C

With 4-methyl-morpholine; n-butyllithium; sodium hexamethyldisilazane; pivaloyl chloride; sodium carbonate; benzotriazol-1-ol; tert-butyldimethylsilyl chloride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dichloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; water;

DOI:10.1021/ja011746f

Reference yield:

3-(4-tert-butoxyphenyl)-propionic acid (21323-98-8) → (2S,3S)-2-[(S)-4-Benzyloxycarbonyl-2-((S)-4-benzyloxycarbonyl-2-{(R)-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-2-methylcarbamoylmethyl-propionylamino}-butyrylamino)-butyrylamino]-3-methyl-pentanoic acid benzyl ester (397883-85-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Et₃N; trimethylacetyl chloride / tetrahydrofuran / 2 h / -15 °C

1.2: 82 percent / lithium chloride / 20 °C

2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: 71 percent / tetrahydrofuran

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 91 percent / tetrahydrofuran / 2 h / -78 - -10 °C

4.1: 98 percent / trifluoroacetic acid / 0.5 h

5.1: 100 percent / Pd/C / ethanol / 0.5 h / 760.05 Torr

6.1: N-methylmorpholine; tert-butyldimethylsilyl chloride / tetrahydrofuran / 1 h / 20 °C

6.2: 1-H-tetrazole / tetrahydrofuran / 20 °C

6.3: 72 percent / tert-butyl hydroperoxide / tetrahydrofuran / -10 - 20 °C

7.1: hydroxybenzotriazole; dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 0 °C

7.2: 67 percent / NMM / tetrahydrofuran / 0 - 20 °C

With 4-methyl-morpholine; n-butyllithium; sodium hexamethyldisilazane; pivaloyl chloride; benzotriazol-1-ol; tert-butyldimethylsilyl chloride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane;

DOI:10.1021/ja011746f

upstream raw materials:

(2R)-2-[4-(bis-benzyloxy-phosphoryloxy)-benzyl]-N-methyl-succinamic acid

(2R)-2-(4-hydroxybenzyl)-N-methyl-succinamic acid benzyl ester

4-tert-butoxybromobenzene

3-(4-tert-butoxyphenyl)-propionic acid

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