4-[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile

Base Information

• Chemical Name: 4-[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile
• CAS No.: 601495-63-0
• Molecular Formula: C₂₀H₂₃NO₇S
• Molecular Weight: 421.471

Synonyms:4-[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile

Chemical Property of 4-[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile

Chemical Property:

Purity/Quality:

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Technology Process of 4-[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile

There total 2 articles about 4-[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile 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: 97.5%

4-cyano-2'-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)acetophenone (601495-36-7) → 4-[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile (601495-63-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(03)00147-2

Reference yield:

4-(1-((Trimethylsilyl)oxy)vinyl)benzonitrile (182058-00-0) → 4-[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile (601495-63-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / Me₃SiOTf / CH₂Cl₂ / 1 h

2: 97.5 percent / NaBH₄ / methanol; CH₂Cl₂

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(03)00147-2

Reference yield: 97.0%

4-[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile (601495-63-0) → [2-(5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile

Guidance literature:

With sodium methylate; In methanol; for 1h;

DOI:10.1016/S0008-6215(03)00147-2

upstream raw materials:

4-cyano-2'-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)acetophenone

4-(1-((Trimethylsilyl)oxy)vinyl)benzonitrile

Downstream raw materials:

[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)ethyl]benzonitrile

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