α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose

Base Information

• Chemical Name: α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose
• CAS No.: 107961-06-8
• Molecular Formula: C₁₆H₂₀O₅S
• Molecular Weight: 324.398

Synonyms:α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose

Chemical Property of α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose

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Technology Process of α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose

There total 5 articles about α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-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: 84.0%

phenyl 2,3-O-isopropylidene-1-thio-α-D-ribofuranoside (153984-49-7) + acetyl chloride (75-36-5) → α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose (107961-06-8)

Guidance literature:

With triethylamine; dmap; In dichloromethane; at -10 ℃; for 0.5h;

DOI:10.1021/ja00244a024

Reference yield: 61.5%

2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose + diphenyldisulfane (882-33-7) → β-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose (107961-05-7) + α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose (107961-06-8)

Guidance literature:

With tributylphosphine; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1021/ja00244a024

Reference yield: 49.5%

1,5-di-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranose (62410-12-2) + thiophenol (108-98-5) → β-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose (107961-05-7) + α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose (107961-06-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/ja00244a024

upstream raw materials:

1,5-di-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranose

thiophenol

phenyl 2,3-O-isopropylidene-1-thio-α-D-ribofuranoside

acetyl chloride

Downstream raw materials:

((3aR,4R,6R,6aR)-2,2-Dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-dimethyl-octyloxy-silane

phenyl 2,3-O-isopropylidene-1-thio-α-D-ribofuranoside

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

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