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

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Chemical Name:N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-seryl-D-glutamic acid 1-methylamide 5-benzyl ester
CAS No.:190587-45-2
Molecular Formula:C₄₈H₅₉N₃O₁₁
Molecular Weight:854.01
Hs Code.:

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

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

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

There total 5 articles about N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-seryl-D-glutamic acid 1-methylamide 5-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: 61.8%

: 127061-08-9
2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride

: 190586-80-2
N-tert-butoxycarbonyl-D-seryl-D-glutamic acid 1-methylamide 5-benzyl ester

: 190587-45-2
N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-seryl-D-glutamic acid 1-methylamide 5-benzyl ester

Guidance literature:: With 4 A molecular sieve; silver trifluoromethanesulfonate; tetramethylurea; tin(ll) chloride; In chloroform; at -50 - 20 ℃; for 21h;
DOI:10.1021/jm970262k

Reference yield:

: 35793-73-8
N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid

: 190587-45-2
N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-seryl-D-glutamic acid 1-methylamide 5-benzyl ester

Guidance literature:: Multi-step reaction with 5 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

With hydrogenchloride; 4 A molecular sieve; silver trifluoromethanesulfonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; tetramethylurea; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jm970262k

Reference yield:

: Kohlensaeureethylester-(S)-(N-BOC)glutaminsaeure-5-benzylesteranhydrid

: 190587-45-2
N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-seryl-D-glutamic acid 1-methylamide 5-benzyl ester

Guidance literature:: Multi-step reaction with 4 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

With hydrogenchloride; 4 A molecular sieve; silver trifluoromethanesulfonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; tetramethylurea; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jm970262k