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

Base Information

• Chemical Name: β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-benzyl-D-ribofuranose
• CAS No.: 107961-14-8
• Molecular Formula: C₃₇H₃₈O₈S
• Molecular Weight: 642.77

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

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

Chemical Property:

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

There total 3 articles about β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-benzyl-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: 4.7%

dimethyl diazomalonate (6773-29-1) + β-1-deoxy-1-C-(phenylthio)-2,3,5-tri-O-benzyl-D-ribofuranose (107961-03-5) → 1-deoxy-1-C--2,3,5-tri-O-benzyl-D-ribofuranose (107961-15-9) + β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-benzyl-D-ribofuranose (107961-14-8)

Guidance literature:

rhodium(II) acetate; In dichloromethane; for 2.5h; Heating;

DOI:10.1021/ja00244a024

Reference yield:

benzyl bromide (100-39-0) → β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-benzyl-D-ribofuranose (107961-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 60percent sodium hydride / dimethylformamide / 15 h / Ambient temperature

2: 4.7 percent / rhodium(II) acetate / CH₂Cl₂ / 2.5 h / Heating

With sodium hydride; rhodium(II) acetate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00244a024

Reference yield:

1-β-(thiophenyl)-3,5-di-O-benzyl-D-ribofuranose (107961-34-2) → β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-benzyl-D-ribofuranose (107961-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 60percent sodium hydride / dimethylformamide / 15 h / Ambient temperature

2: 4.7 percent / rhodium(II) acetate / CH₂Cl₂ / 2.5 h / Heating

With sodium hydride; rhodium(II) acetate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00244a024

upstream raw materials:

dimethyl diazomalonate

β-1-deoxy-1-C-(phenylthio)-2,3,5-tri-O-benzyl-D-ribofuranose

benzyl bromide

1-β-(thiophenyl)-3,5-di-O-benzyl-D-ribofuranose

Downstream raw materials:

1-deoxy-1-C--2,3,5-tri-O-benzyl-D-ribofuranose

α-1-deoxy-1-C--2,3,5-tri-O-benzyl-D-ribofuranose

β-1-deoxy-1-C--2,3,5-tri-O-benzyl-D-ribofuranose

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