N-(1-{(2S,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide

Base Information

• Chemical Name: N-(1-{(2S,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide
• CAS No.: 200562-16-9
• Molecular Formula: C₃₇H₃₅N₃O₈
• Molecular Weight: 649.7
• Mol file: 200562-16-9.mol

Synonyms:

Chemical Property of N-(1-{(2S,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(1-{(2S,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide

There total 3 articles about N-(1-{(2S,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide 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:

(3S,4R,5S)-5-Triisopropylsilanyloxymethyl-tetrahydro-furan-2,3,4-triol → N-(1-{(2S,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide (200562-16-9)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂; pyridine / 14 h / Ambient temperature

2: 1.) BSA, SnCl₄; 2.) conc. aq. HCl / 1.) MeCN, 60 deg C, 1 h; 2.) THF, r.t., 2 h

3: 1.) (i-Pr)2NEt; 2.) 10N aq. NaOH / 1.) CH₂Cl₂, r.t., 30 min; 2.) CH₂Cl₂, THF, MeOH, 4 deg C, 25 min

With hydrogenchloride; benzenesulfonamide; sodium hydroxide; tin(IV) chloride; N-ethyl-N,N-diisopropylamine; In pyridine; dichloromethane;

DOI:10.1002/hlca.19970800803

Reference yield:

1,2,3-tri-O-benzoyl-5-O-(triisopropylsilyl)-α/β-L-ribose → N-(1-{(2S,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide (200562-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BSA, SnCl₄; 2.) conc. aq. HCl / 1.) MeCN, 60 deg C, 1 h; 2.) THF, r.t., 2 h

2: 1.) (i-Pr)2NEt; 2.) 10N aq. NaOH / 1.) CH₂Cl₂, r.t., 30 min; 2.) CH₂Cl₂, THF, MeOH, 4 deg C, 25 min

With hydrogenchloride; benzenesulfonamide; sodium hydroxide; tin(IV) chloride; N-ethyl-N,N-diisopropylamine;

DOI:10.1002/hlca.19970800803

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) + N4-benzoyl-1-(2',3'-di-O-benzoyl-β-L-ribofuranosyl)cytosine (200562-11-4) → N-(1-{(2S,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide (200562-16-9)

Guidance literature:

With sodium hydroxide; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, r.t., 30 min; 2.) CH₂Cl₂, THF, MeOH, 4 deg C, 25 min;

DOI:10.1002/hlca.19970800803

upstream raw materials:

4,4'-dimethoxytrityl chloride

N⁴-benzoyl-1-(2',3'-di-O-benzoyl-β-L-ribofuranosyl)cytosine

Downstream raw materials:

Heptanedioic acid (2S,3S,4S,5S)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-3-yl ester 4-nitro-phenyl ester

Diisopropyl-phosphoramidous acid (2S,3S,4S,5S)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Diisopropyl-phosphoramidous acid (2S,3S,4S,5S)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

N-{1-[(2S,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-4-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide