C1′-epi-digitoxin

Base Information

• Chemical Name: C1′-epi-digitoxin
• CAS No.: 1512847-12-9
• Molecular Formula: C₄₁H₆₄O₁₃
• Molecular Weight: 764.951

Synonyms:C1′-epi-digitoxin

Chemical Property of C1′-epi-digitoxin

Chemical Property:

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Technology Process of C1′-epi-digitoxin

There total 19 articles about C1′-epi-digitoxin 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:

C65H120O13Si4 → C1′-epi-digitoxin (1512847-12-9) + digitoxin (71-63-6)

Guidance literature:

With ammonium fluoride-hydrogen fluoride; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; at 70 ℃; for 4h; Overall yield = 90 %; Overall yield = 11 mg;

DOI:10.1021/jo4021419

Reference yield:

C65H120O13Si4 → C1′-epi-digitoxin (1512847-12-9) + digitoxin (71-63-6)

Guidance literature:

With ammonium fluoride-hydrogen fluoride; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; at 80 ℃; for 144h; Overall yield = 85 %; Overall yield = 11 mg;

DOI:10.1021/jo4021419

Reference yield:

1,5-anhydro-3-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,6-dideoxy-D-ribo-hex-1-enitol → C1′-epi-digitoxin (1512847-12-9) + digitoxin (71-63-6)

Guidance literature:

Multi-step reaction with 5 steps

1: [ReOCl₃(OPPh₃)(SMe₂)] / benzene / 60 h / 0 °C

2: lithium 4,4′-di(tert-butyl)biphenyl / tetrahydrofuran / 0.25 h / -20 °C

3: 1H-imidazole / N,N-dimethyl-formamide / 40 h / 20 - 50 °C

4: triphenylphosphine hydrobromide / chloroform / 24 h / 20 °C / Molecular sieve

5: ammonium fluoride-hydrogen fluoride / N,N-dimethyl-formamide; 1-methyl-pyrrolidin-2-one / 144 h / 80 °C

With 1H-imidazole; ammonium fluoride-hydrogen fluoride; lithium 4,4′-di(tert-butyl)biphenyl; [ReOCl₃(OPPh₃)(SMe₂)]; triphenylphosphine hydrobromide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; chloroform; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo4021419

upstream raw materials:

phenyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribohexapyranosyl-(1→4)-3-O-benzyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-ribohexopyranoside

2,6-dideoxy-3,4-bis-O-(triethylsilyl)-β-D-ribohexapyranosyl-(1→4)-2,6-dideoxy-3-O-triethylsilyl-β-D-ribo-hexapyranosyl-(1→4)-1,5-anhydro-2,6-dideoxy-3-O-triethylsilyl-D-ribo-hex-1-enitol

3,4-Di-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribohexapyranosyl-(1→4)-1,5-anhydro-3-O-tert-butyldimethylsilyl-2,6-dideoxy-D-ribo-hex-1-enitol

1,2,4,6-tetra-O-acetyl-3-O-benzylallopyranose

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