(2S)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile

Base Information

• Chemical Name: (2S)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile
• CAS No.: 60981-45-5
• Molecular Formula: C₂₄H₂₇NO₁₂
• Molecular Weight: 521.478
• Mol file: 60981-45-5.mol

Synonyms:(2S)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile

Chemical Property of (2S)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile

There total 2 articles about (2S)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile 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:

2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosyl fluoride (162489-61-4) + C13H17NO3Si (118736-06-4) → (2S)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile (60981-45-5) + (2R)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile (60996-21-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.5b01121

Reference yield:

→ (2S)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile (60981-45-5)

Guidance literature:

Dhurrin, Acetanhydrid-Pyridin, Raumtemp.;

DOI:10.1016/S0040-4020(01)98398-X

Reference yield:

(2S)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile (60981-45-5) → (2S)-2-(β-D-glucopyranosyloxy)-4-hydroxyphenylacetonitrile (499-20-7)

Guidance literature:

With methanol; trifluorormethanesulfonic acid; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.5b01121

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosyl fluoride

C₁₃H₁₇NO₃Si

Downstream raw materials:

(2S)-2-(β-D-glucopyranosyloxy)-4-hydroxyphenylacetonitrile