4,5,6-tri-O-benzyl-2,3-dideoxy-3-{[(dibenzyloxyphosphoryl)methyl]amino}-2-(trifluoroacetamido)-D-mannono-1,3-lactam

Base Information

Chemical Name:4,5,6-tri-O-benzyl-2,3-dideoxy-3-{[(dibenzyloxyphosphoryl)methyl]amino}-2-(trifluoroacetamido)-D-mannono-1,3-lactam
CAS No.:259792-37-5
Molecular Formula:C₄₄H₄₄F₃N₂O₈P
Molecular Weight:816.811
Hs Code.:

Synonyms:4,5,6-tri-O-benzyl-2,3-dideoxy-3-{[(dibenzyloxyphosphoryl)methyl]amino}-2-(trifluoroacetamido)-D-mannono-1,3-lactam

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Chemical Property of 4,5,6-tri-O-benzyl-2,3-dideoxy-3-{[(dibenzyloxyphosphoryl)methyl]amino}-2-(trifluoroacetamido)-D-mannono-1,3-lactam

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Technology Process of 4,5,6-tri-O-benzyl-2,3-dideoxy-3-{[(dibenzyloxyphosphoryl)methyl]amino}-2-(trifluoroacetamido)-D-mannono-1,3-lactam

There total 8 articles about 4,5,6-tri-O-benzyl-2,3-dideoxy-3-{[(dibenzyloxyphosphoryl)methyl]amino}-2-(trifluoroacetamido)-D-mannono-1,3-lactam 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: 89.0%

: 407-25-0
trifluoroacetic anhydride

: 259792-36-4
2-azido-4,5,6-tri-O-benzyl-2,3-dideoxy-3-{[(dibenzyloxyphosphoryl)methyl]amino}-D-mannono-1,3-lactam

: 259792-37-5
4,5,6-tri-O-benzyl-2,3-dideoxy-3-{[(dibenzyloxyphosphoryl)methyl]amino}-2-(trifluoroacetamido)-D-mannono-1,3-lactam

Guidance literature:: With water; 3,4-dihydro-pyrido[1,2-a]pyrimidin-2-one; triphenylphosphine; In tetrahydrofuran; for 27h;
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2380::AID-HLCA2380>3.0.CO;2-P

Reference yield:

: 100-39-0
benzyl bromide

: 259792-37-5
4,5,6-tri-O-benzyl-2,3-dideoxy-3-{[(dibenzyloxyphosphoryl)methyl]amino}-2-(trifluoroacetamido)-D-mannono-1,3-lactam

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / Bu₄NI / dimethylformamide / 5 h / 0 - 22 °C

2.1: 86 percent / H₂O; CuCl₂; CuO / acetone / 3 h / Heating

3.1: molecular sieves (3A) / CH₂Cl₂ / 4 h / 0 °C

4.1: iPr₂EtN / CH₂Cl₂ / 19 h / 24 °C

4.2: LiN₃; 1,3-dimethylimidazolidin-2-one / 69 h / 50 - 70 °C

4.3: ceric ammonium nitrate / acetonitrile; H₂O / 2.33 h / -20 - -15 °C

5.1: 55 percent / NaH; 1,3-dimethylimidazolidin-2-one; 12-crown-4 / tetrahydrofuran / 2 h / -30 - 0 °C

6.1: 89 percent / PPh₃; 3,4-dihydropyrido[2,1-b]pyrimidin-2(2H)-one; H₂O / tetrahydrofuran / 27 h

With 1,3-dimethyl-2-imidazolidinone; (1,4,7,10-tetraoxacyclododecane); 3 A molecular sieve; water; tetra-(n-butyl)ammonium iodide; sodium hydride; 3,4-dihydro-pyrido[1,2-a]pyrimidin-2-one; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(II) oxide; copper dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: benzylation / 2.1: Hydrolysis / 3.1: Condensation / 4.1: cyclocondensation / 4.2: Substitution / 4.3: N-dearylation / 5.1: Substitution / 6.1: Reduction;
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2380::AID-HLCA2380>3.0.CO;2-P

Reference yield:

: 114790-35-1
dibenzyl hydroxymethylphosphonate

: 259792-37-5
4,5,6-tri-O-benzyl-2,3-dideoxy-3-{[(dibenzyloxyphosphoryl)methyl]amino}-2-(trifluoroacetamido)-D-mannono-1,3-lactam

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / iPr₃N / CH₂Cl₂ / 2.5 h / -70 - -25 °C

2: 55 percent / NaH; 1,3-dimethylimidazolidin-2-one; 12-crown-4 / tetrahydrofuran / 2 h / -30 - 0 °C

3: 89 percent / PPh₃; 3,4-dihydropyrido[2,1-b]pyrimidin-2(2H)-one; H₂O / tetrahydrofuran / 27 h

With 1,3-dimethyl-2-imidazolidinone; (1,4,7,10-tetraoxacyclododecane); triisopropylamine; water; sodium hydride; 3,4-dihydro-pyrido[1,2-a]pyrimidin-2-one; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1: Acylation / 2: Substitution / 3: Reduction;
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2380::AID-HLCA2380>3.0.CO;2-P