N-phenylacetoxybenzyloxycarbonyl-L-prolyl-L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl ester

Base Information

Chemical Name:N-phenylacetoxybenzyloxycarbonyl-L-prolyl-L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl ester
CAS No.:333362-85-9
Molecular Formula:C₅₃H₆₆N₇O₁₉P
Molecular Weight:1136.12
Hs Code.:

N-phenylacetoxybenzyloxycarbonyl-L-prolyl-L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl ester

Synonyms:N-phenylacetoxybenzyloxycarbonyl-L-prolyl-L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl ester

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Chemical Property of N-phenylacetoxybenzyloxycarbonyl-L-prolyl-L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl ester

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Technology Process of N-phenylacetoxybenzyloxycarbonyl-L-prolyl-L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl ester

There total 9 articles about N-phenylacetoxybenzyloxycarbonyl-L-prolyl-L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl 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: 85.0%

: 192999-61-4
PhAcOZ-Pro-OH

: 333362-84-8
L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl ester

: 333362-85-9
N-phenylacetoxybenzyloxycarbonyl-L-prolyl-L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl ester

Guidance literature:: With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1002/1521-3765(20020415)8:8<1879::AID-CHEM1879>3.0.CO;2-5

Reference yield:

: 192999-59-0
PhAcOZ-Val-OH

: 333362-85-9
N-phenylacetoxybenzyloxycarbonyl-L-prolyl-L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / HATU; DIPEA / dimethylformamide / 1 h / 0 °C

2: (iPr)2NH; tetrazole / CH₂Cl₂ / 1 h / 0 °C

3: terazole / acetonitrile; CH₂Cl₂ / 24 h / 20 °C

4: t-BuOOH / acetonitrile; CH₂Cl₂ / 0.17 h / 0 °C

5: 60 percent / penicillin G acylase; aq. KI / aq. phosphate buffer; methanol / 24 h / 20 °C / pH 6.8

6: 85 percent / HATU / dimethylformamide / 1 h / 20 °C

With 1H-tetrazole; tert.-butylhydroperoxide; penicillin G acylase; terazole; diisopropylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium iodide; In methanol; phosphate buffer; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/1521-3765(20020415)8:8<1879::AID-CHEM1879>3.0.CO;2-5

Reference yield:

: 357625-71-9
{1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester

: 333362-85-9
N-phenylacetoxybenzyloxycarbonyl-L-prolyl-L-valinyl-L-seryl-O-(3'-O-acetyl-6-N-allyloxycarbonyl-2'-deoxycytidyl-allyl-phosphato)-L-alanine allyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / pyridine / 3 h / 20 °C

2: 98 percent / Bu₄NF / tetrahydrofuran / 3 h / 20 °C

3: terazole / acetonitrile; CH₂Cl₂ / 24 h / 20 °C

4: t-BuOOH / acetonitrile; CH₂Cl₂ / 0.17 h / 0 °C

5: 60 percent / penicillin G acylase; aq. KI / aq. phosphate buffer; methanol / 24 h / 20 °C / pH 6.8

6: 85 percent / HATU / dimethylformamide / 1 h / 20 °C

With pyridine; tert.-butylhydroperoxide; penicillin G acylase; terazole; tetrabutyl ammonium fluoride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium iodide; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/1521-3765(20020415)8:8<1879::AID-CHEM1879>3.0.CO;2-5