phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside

Base Information

• Chemical Name: phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside
• CAS No.: 91510-80-4
• Molecular Formula: C₂₀H₃₂O₄SSi
• Molecular Weight: 396.623
• Mol file: 91510-80-4.mol

Synonyms:phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside

Chemical Property of phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside

There total 2 articles about phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside 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: 90.0%

5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranose (75921-20-9) + diphenyldisulfane (882-33-7) → phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside (91510-80-4)

Guidance literature:

With triethylphosphine; In acetonitrile; for 1h; Ambient temperature;

Reference yield: 71.0%

5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose (217309-46-1) + diphenyldisulfane (882-33-7) → phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside (91510-80-4)

Guidance literature:

With tributylphosphine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1055/s-2008-1067226

Reference yield:

phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside (91510-80-4) → 5-O-tert-butyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-1-[(Rs)-phenylsulfinyl]-α-D-ribofuranose (1092982-05-2) + 5-O-tert-butyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-1-[(Ss)-phenylsulfinyl]-α-D-ribofuranose (1092981-93-5)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1055/s-2008-1067226

upstream raw materials:

5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranose

diphenyldisulfane

5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

Downstream raw materials:

5-O-tert-butyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-1-[(Rs)-phenylsulfinyl]-α-D-ribofuranose

5-O-tert-butyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-1-[(Ss)-phenylsulfinyl]-α-D-ribofuranose