(R)-4-Methylcarbamoyl-4-[(R)-2-(2-tetradecyl-hexadecanoylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-butyric acid benzyl ester

Base Information

• Chemical Name: (R)-4-Methylcarbamoyl-4-[(R)-2-(2-tetradecyl-hexadecanoylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-butyric acid benzyl ester
• CAS No.: 190587-52-1
• Molecular Formula: C₇₃H₁₀₉N₃O₁₀
• Molecular Weight: 1188.68

Synonyms:

Chemical Property of (R)-4-Methylcarbamoyl-4-[(R)-2-(2-tetradecyl-hexadecanoylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-Methylcarbamoyl-4-[(R)-2-(2-tetradecyl-hexadecanoylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-butyric acid benzyl ester

There total 6 articles about (R)-4-Methylcarbamoyl-4-[(R)-2-(2-tetradecyl-hexadecanoylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-butyric 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:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid (35793-73-8) → (R)-4-Methylcarbamoyl-4-[(R)-2-(2-tetradecyl-hexadecanoylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-butyric acid benzyl ester (190587-52-1)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N / tetrahydrofuran / 0.03 h / 0 °C

2: tetrahydrofuran; methanol / 2 h / 0 - 20 °C

3: 4 N HCl / dioxane / 0.5 h / Ambient temperature

4: WSC, HOBt / dimethylformamide / 18 h / Ambient temperature

5: 61.8 percent / AgOTf, SnCl₂, TMU, 4 Angstroem molecular sieves / CHCl₃ / 21 h / -50 - 20 °C

6: TFA / CH₂Cl₂ / 2 h / Ambient temperature

7: WSC, HOBt / dimethylformamide / 20 h

With hydrogenchloride; 4 A molecular sieve; silver trifluoromethanesulfonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; tetramethylurea; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm970262k

Reference yield:

Kohlensaeureethylester-(S)-(N-BOC)glutaminsaeure-5-benzylesteranhydrid → (R)-4-Methylcarbamoyl-4-[(R)-2-(2-tetradecyl-hexadecanoylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-butyric acid benzyl ester (190587-52-1)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran; methanol / 2 h / 0 - 20 °C

2: 4 N HCl / dioxane / 0.5 h / Ambient temperature

3: WSC, HOBt / dimethylformamide / 18 h / Ambient temperature

4: 61.8 percent / AgOTf, SnCl₂, TMU, 4 Angstroem molecular sieves / CHCl₃ / 21 h / -50 - 20 °C

5: TFA / CH₂Cl₂ / 2 h / Ambient temperature

6: WSC, HOBt / dimethylformamide / 20 h

With hydrogenchloride; 4 A molecular sieve; silver trifluoromethanesulfonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; tetramethylurea; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm970262k

Reference yield:

N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-seryl-D-glutamic acid 1-methylamide 5-benzyl ester (190587-45-2) → (R)-4-Methylcarbamoyl-4-[(R)-2-(2-tetradecyl-hexadecanoylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-butyric acid benzyl ester (190587-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 2 h / Ambient temperature

2: WSC, HOBt / dimethylformamide / 20 h

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970262k

upstream raw materials:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid

N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-seryl-D-glutamic acid 1-methylamide 5-benzyl ester

(R)-4-Amino-4-methylcarbamoyl-butyric acid benzyl ester

benzyl N²-(tert-butoxycarbonyl)-N¹-methyl-D-glutaminate

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