N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-L-seryl-L-proline methyl ester

Base Information

Chemical Name:N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-L-seryl-L-proline methyl ester
CAS No.:158975-43-0
Molecular Formula:C₂₉H₃₈N₂O₁₄
Molecular Weight:638.626
Hs Code.:

Synonyms:N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-L-seryl-L-proline methyl ester

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Chemical Property of N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-L-seryl-L-proline methyl ester

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Technology Process of N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-L-seryl-L-proline methyl ester

There total 5 articles about N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-L-seryl-L-proline methyl 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: 79.3%

: 158975-51-0
N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-6-O-trityl-α-D-mannopyranosyl)-(1<*>3)-L-seryl-L-proline methyl ester

: 158975-43-0
N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-L-seryl-L-proline methyl ester

Guidance literature:: With acetic acid; at 55 ℃; for 6h;
DOI:10.1016/0008-6215(94)84227-2

Reference yield:

: 1145-80-8
N-(benzyloxycarbonyl)-L-serine

: 158975-43-0
N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-L-seryl-L-proline methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 36.3 percent / Et₃N, diethylphosphorocyanidate / CH₂Cl₂; dimethylformamide / 24 h / 0 - 20 °C

2: 52.3 percent / Hg(CN)2, HgBr₂, 4A molecular sieves / 42 h / Ambient temperature

3: 67.4 percent / NaOMe / methanol / 6.5 h / 0 °C

4: pyridine / 30 h / 70 °C

5: pyridine / 0 - 20 °C

6: 79.3 percent / 80percent aq. AcOH / 6 h / 55 °C

With pyridine; diethyl cyanophosphonate; 4 A molecular sieve; sodium methylate; mercury(II) cyanide; acetic acid; triethylamine; mercury dibromide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(94)84227-2

Reference yield:

: 2133-40-6
L-proline methyl ester monohydrochloride

: 158975-43-0
N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-L-seryl-L-proline methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 36.3 percent / Et₃N, diethylphosphorocyanidate / CH₂Cl₂; dimethylformamide / 24 h / 0 - 20 °C

2: 52.3 percent / Hg(CN)2, HgBr₂, 4A molecular sieves / 42 h / Ambient temperature

3: 67.4 percent / NaOMe / methanol / 6.5 h / 0 °C

4: pyridine / 30 h / 70 °C

5: pyridine / 0 - 20 °C

6: 79.3 percent / 80percent aq. AcOH / 6 h / 55 °C

With pyridine; diethyl cyanophosphonate; 4 A molecular sieve; sodium methylate; mercury(II) cyanide; acetic acid; triethylamine; mercury dibromide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(94)84227-2