3-[[2-(Acetyl-methyl-amino)-acetyl]-({({benzyl-[(tert-butoxycarbonylmethyl-isopropyl-carbamoyl)-methyl]-carbamoyl}-methyl)-[2-((2R,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-ethyl]-carbamoyl}-methyl)-amino]-propionic acid tert-butyl ester

Base Information

• Chemical Name: 3-[[2-(Acetyl-methyl-amino)-acetyl]-({({benzyl-[(tert-butoxycarbonylmethyl-isopropyl-carbamoyl)-methyl]-carbamoyl}-methyl)-[2-((2R,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-ethyl]-carbamoyl}-methyl)-amino]-propionic acid tert-butyl ester
• CAS No.: 189056-62-0
• Molecular Formula: C₄₁H₆₅N₅O₁₄
• Molecular Weight: 851.992

Synonyms:

Chemical Property of 3-[[2-(Acetyl-methyl-amino)-acetyl]-({({benzyl-[(tert-butoxycarbonylmethyl-isopropyl-carbamoyl)-methyl]-carbamoyl}-methyl)-[2-((2R,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-ethyl]-carbamoyl}-methyl)-amino]-propionic acid tert-butyl ester

Chemical Property:

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MSDS Files:

Useful:

Technology Process of 3-[[2-(Acetyl-methyl-amino)-acetyl]-({({benzyl-[(tert-butoxycarbonylmethyl-isopropyl-carbamoyl)-methyl]-carbamoyl}-methyl)-[2-((2R,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-ethyl]-carbamoyl}-methyl)-amino]-propionic acid tert-butyl ester

There total 18 articles about 3-[[2-(Acetyl-methyl-amino)-acetyl]-({({benzyl-[(tert-butoxycarbonylmethyl-isopropyl-carbamoyl)-methyl]-carbamoyl}-methyl)-[2-((2R,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-ethyl]-carbamoyl}-methyl)-amino]-propionic acid tert-butyl 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:

phenyl 1-thio-β-D-xylopyranoside (20452-28-2,64244-01-5,105026-42-4,122604-15-3) → 3-[[2-(Acetyl-methyl-amino)-acetyl]-({({benzyl-[(tert-butoxycarbonylmethyl-isopropyl-carbamoyl)-methyl]-carbamoyl}-methyl)-[2-((2R,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-ethyl]-carbamoyl}-methyl)-amino]-propionic acid tert-butyl ester (189056-62-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / pyridine / 1.5 h / Ambient temperature

2: 78 percent / DMTST / CH₂Cl₂ / 1.) 0 deg C, 7 h, 2.) room temperature, 18 h

3: 95 percent / H₂ / Pd-C / methanol

4: 47 percent / DIPEA / acetonitrile / 1 h / 0 °C

5: 92 percent / DCC / CH₂Cl₂ / 2 h / Ambient temperature

6: NaOCH₃ / methanol / 2 h / Ambient temperature; pH 9

With pyridine; hydrogen; sodium methylate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0008-6215(96)00301-1

Reference yield:

N-acetylsarcosine (5888-91-5) → 3-[[2-(Acetyl-methyl-amino)-acetyl]-({({benzyl-[(tert-butoxycarbonylmethyl-isopropyl-carbamoyl)-methyl]-carbamoyl}-methyl)-[2-((2R,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-ethyl]-carbamoyl}-methyl)-amino]-propionic acid tert-butyl ester (189056-62-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / DCC / CH₂Cl₂ / 5 h / Ambient temperature

2: 98 percent / H₂ / Pd-C / methanol / 3 h

3: 92 percent / DCC / CH₂Cl₂ / 2 h / Ambient temperature

4: NaOCH₃ / methanol / 2 h / Ambient temperature; pH 9

With hydrogen; sodium methylate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(96)00301-1

Reference yield:

N-acetyl-t-butoxysarcosine (168553-60-4) → 3-[[2-(Acetyl-methyl-amino)-acetyl]-({({benzyl-[(tert-butoxycarbonylmethyl-isopropyl-carbamoyl)-methyl]-carbamoyl}-methyl)-[2-((2R,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-ethyl]-carbamoyl}-methyl)-amino]-propionic acid tert-butyl ester (189056-62-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / TFA / CH₂Cl₂ / 2 h / Ambient temperature

2: 98 percent / DCC / CH₂Cl₂ / 5 h / Ambient temperature

3: 98 percent / H₂ / Pd-C / methanol / 3 h

4: 92 percent / DCC / CH₂Cl₂ / 2 h / Ambient temperature

5: NaOCH₃ / methanol / 2 h / Ambient temperature; pH 9

With hydrogen; sodium methylate; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(96)00301-1

upstream raw materials:

C₆₂H₇₇N₅O₁₇

phenyl 1-thio-β-D-xylopyranoside

bromoacetic acid tert-butyl ester

N-acetylsarcosine

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