(S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester

Base Information

Chemical Name:(S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester
CAS No.:190587-21-4
Molecular Formula:C₄₃H₅₁N₃O₉
Molecular Weight:753.893
Hs Code.:

(S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester

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Chemical Property of (S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester

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Technology Process of (S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester

There total 3 articles about (S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-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:

: 190587-03-2
[N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester

: 190587-21-4
(S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1021/jm9707481

Reference yield:

: 82594-35-2
(S)-4-Amino-4-methylcarbamoyl-butyric acid benzyl ester

: 190587-21-4
(S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) 4N HCl in dioxane, 2.) Et₃N, 3.) WSC, HOBt

2: 20.5 percent / 4A molecular sieves, AgOTf, SnCl₂, TMU / CH₂Cl₂ / 20 h / -50 - 20 °C

3: TFA / CH₂Cl₂ / 2 h / Ambient temperature

With hydrogenchloride; 4 A molecular sieve; silver trifluoromethanesulfonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; tetramethylurea; tin(ll) chloride; In dichloromethane;
DOI:10.1021/jm9707481

Reference yield:

: 190586-78-8
N-tert-butoxycarbonyl-D-seryl-L-glutamic acid 1-methylamide 5-benzyl ester

: 190587-21-4
(S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 20.5 percent / 4A molecular sieves, AgOTf, SnCl₂, TMU / CH₂Cl₂ / 20 h / -50 - 20 °C

2: TFA / CH₂Cl₂ / 2 h / Ambient temperature

With 4 A molecular sieve; silver trifluoromethanesulfonate; trifluoroacetic acid; tetramethylurea; tin(ll) chloride; In dichloromethane;
DOI:10.1021/jm9707481