allyl 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 phosphite

Base Information

• Chemical Name: allyl 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 phosphite
• CAS No.: 194665-67-3
• Molecular Formula: C₄₄H₅₅N₄O₂₃P
• Molecular Weight: 1038.91

Synonyms:allyl 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 phosphite

Chemical Property of allyl 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 phosphite

Chemical Property:

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Technology Process of allyl 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 phosphite

There total 7 articles about allyl 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 phosphite 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: 43.0%

2-allyl-2'-(2',3',N4-triacetyl-cytidin-5')-yl-N,N'-diisopropylphosphoramidite (188786-02-9) + methyl (4,7,8,9-tetra-O-acetyl-5-amino-5-N-benzyloxycarbonyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate (194665-64-0) → allyl 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 phosphite (194665-67-3)

Guidance literature:

With triethylamine; In acetonitrile; -43 deg C -> room temperature;

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) → allyl 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 phosphite (194665-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1: conc. HCl, AcCl / CH₂Cl₂ / 65 h

2: Ag₂CO₃ / acetone; H₂O / 48 h

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

With hydrogenchloride; triethylamine; 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) → allyl 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 phosphite (194665-67-3)

Guidance literature:

Multi-step reaction with 4 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

With N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;

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

upstream raw materials:

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

methyl (4,7,8,9-tetra-O-acetyl-5-amino-5-N-benzyloxycarbonyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate

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

Downstream raw materials:

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

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

C₄₄H₅₅N₄O₂₄P

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