β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose

Base Information

• Chemical Name: β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose
• CAS No.: 107961-13-7
• Molecular Formula: C₂₂H₂₆O₁₁S
• Molecular Weight: 498.508
• Mol file: 107961-13-7.mol

Synonyms:β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose

Chemical Property of β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose

There total 1 articles about β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose 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: 70.7%

dimethyl diazomalonate (6773-29-1) + phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside (52544-88-4) → β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose (107961-13-7)

Guidance literature:

rhodium(II) acetate; In dichloromethane; for 2h; Heating;

DOI:10.1021/ja00244a024

Reference yield: 40.0%

β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose (107961-13-7) → methyl 2-(phenylthio)-2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-acetate (107961-30-8,107961-39-7)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; dimethylsulfide; Celite; In benzene; for 24h; Heating;

DOI:10.1021/ja00244a024

Reference yield:

β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose (107961-13-7) → methyl 2-(phenylsulfinyl)-2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-acetate (107961-31-9,107961-40-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / DABCO, Me₂S, celite / benzene / 24 h / Heating

2: 91.6 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 2 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; dimethylsulfide; Celite; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; benzene;

DOI:10.1021/ja00244a024

upstream raw materials:

dimethyl diazomalonate

phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside

Downstream raw materials:

methyl 2-(phenylthio)-2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-acetate

methyl 2-(phenylsulfinyl)-2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-acetate