2',3'-O,N⁴-triacetylcytidin-5'-yl methyl 4,7,8,9-tetra-O-acetyl-5-amino-5-N-benzyloxycarbonyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphate

Base Information

• Chemical Name: 2',3'-O,N⁴-triacetylcytidin-5'-yl methyl 4,7,8,9-tetra-O-acetyl-5-amino-5-N-benzyloxycarbonyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphate
• CAS No.: 194665-69-5
• Molecular Formula: C₄₁H₅₁N₄O₂₄P
• Molecular Weight: 1014.84

Synonyms:

Chemical Property of 2',3'-O,N⁴-triacetylcytidin-5'-yl methyl 4,7,8,9-tetra-O-acetyl-5-amino-5-N-benzyloxycarbonyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphate

Chemical Property:

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Useful:

Technology Process of 2',3'-O,N⁴-triacetylcytidin-5'-yl methyl 4,7,8,9-tetra-O-acetyl-5-amino-5-N-benzyloxycarbonyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphate

There total 10 articles about 2',3'-O,N⁴-triacetylcytidin-5'-yl methyl 4,7,8,9-tetra-O-acetyl-5-amino-5-N-benzyloxycarbonyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphate 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:

C44H55N4O24P (220765-73-1) → 2',3'-O,N4-triacetylcytidin-5'-yl methyl 4,7,8,9-tetra-O-acetyl-5-amino-5-N-benzyloxycarbonyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphate (194665-69-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine; In acetonitrile; for 0.5h; Yield given;

DOI:10.1016/S0040-4020(97)00370-0

Reference yield:

2,4,7,8,9-penta-O-acetyl-5-N-carbobenzoxylamino-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulo-pyranosidonic acid methyl ester (146669-04-7) → 2',3'-O,N4-triacetylcytidin-5'-yl methyl 4,7,8,9-tetra-O-acetyl-5-amino-5-N-benzyloxycarbonyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphate (194665-69-5)

Guidance literature:

Multi-step reaction with 5 steps

1: conc. HCl, AcCl / CH₂Cl₂ / 65 h

2: Ag₂CO₃ / acetone; H₂O / 48 h

3: 43 percent / Et₃N / acetonitrile / -43 deg C -> room temperature

4: Et₃N, t-BuOOH / acetonitrile / 1 h / Ambient temperature

5: iPr₂NH, (Ph₃P)4Pd / acetonitrile / 0.5 h

With hydrogenchloride; tert.-butylhydroperoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; diisopropylamine; acetyl chloride; silver carbonate; In dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0040-4020(97)00370-0

Reference yield:

5'-O-(tert-butyldiphenylsilyl)cytidine (58479-65-5) → 2',3'-O,N4-triacetylcytidin-5'-yl methyl 4,7,8,9-tetra-O-acetyl-5-amino-5-N-benzyloxycarbonyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphate (194665-69-5)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 12 h

2: 94 percent / n-Bu₄NF, AcOH / tetrahydrofuran / 18 h / Ambient temperature

3: 61 percent / diisopropylammoniumtetrazole / CH₂Cl₂ / 2 h

4: 43 percent / Et₃N / acetonitrile / -43 deg C -> room temperature

5: Et₃N, t-BuOOH / acetonitrile / 1 h / Ambient temperature

6: iPr₂NH, (Ph₃P)4Pd / acetonitrile / 0.5 h

With tert.-butylhydroperoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; acetic acid; triethylamine; diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(97)00370-0

upstream raw materials:

C₄₄H₅₅N₄O₂₄P

2,4,7,8,9-penta-O-acetyl-5-N-carbobenzoxylamino-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulo-pyranosidonic acid methyl ester

5'-O-(tert-butyldiphenylsilyl)cytidine

2-allyl-2'-(2',3',N⁴-triacetyl-cytidin-5')-yl-N,N'-diisopropylphosphoramidite

Downstream raw materials:

cytidin-5'-yl 5-N-carbobenzyloxyamino-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid-2''-yl phosphate

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