(-)-(2E)-3-[4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxy-phenyl]-2-methylacrylic acid

Base Information

• Chemical Name: (-)-(2E)-3-[4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxy-phenyl]-2-methylacrylic acid
• CAS No.: 1410798-41-2
• Molecular Formula: C₃₄H₅₈O₈Si₂
• Molecular Weight: 651.001
• Mol file: 1410798-41-2.mol

Synonyms:(-)-(2E)-3-[4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxy-phenyl]-2-methylacrylic acid

Chemical Property of (-)-(2E)-3-[4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxy-phenyl]-2-methylacrylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2E)-3-[4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxy-phenyl]-2-methylacrylic acid

There total 5 articles about (-)-(2E)-3-[4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxy-phenyl]-2-methylacrylic acid 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: 61.0%

methyl (2E)-3-[3-(allyloxy)-4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-D-arabinohexofuranosyl-5-ulose]oxy}phenyl]-2-methylacrylate → (-)-(2E)-3-[4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxy-phenyl]-2-methylacrylic acid (1410798-41-2)

Guidance literature:

methyl (2E)-3-[3-(allyloxy)-4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-D-arabinohexofuranosyl-5-ulose]oxy}phenyl]-2-methylacrylate; With aluminum tri-bromide; dimethylsulfide; In dichloromethane; at 5 - 10 ℃;

With water; rochelle salt; In dichloromethane;

DOI:10.1002/anie.200902840

Reference yield: 61.0%

(-)-(2E)-3-[3-(allyloxy)-4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabinohexofuranosyl-5-ulose]oxy}phenyl]-2-methylacrylate → (-)-(2E)-3-[4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxy-phenyl]-2-methylacrylic acid (1410798-41-2)

Guidance literature:

With aluminum tri-bromide; dimethylsulfide; In dichloromethane; at 5 - 10 ℃; for 5.5h; Inert atmosphere;

DOI:10.1021/ol3028237

Reference yield:

(E)-methyl 3-(3-(allyloxy)-4-hydroxyphenyl)-2-methylacrylate (1190266-98-8) → (-)-(2E)-3-[4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxy-phenyl]-2-methylacrylic acid (1410798-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 3 h / 60 °C / Inert atmosphere

2: dimethylsulfide; aluminum tri-bromide / dichloromethane / 5.5 h / 5 - 10 °C / Inert atmosphere

With aluminum tri-bromide; dimethylsulfide; di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; toluene; 1: |Mitsunobu Displacement;

DOI:10.1021/ol3028237

upstream raw materials:

(E)-methyl 3-(3-(allyloxy)-4-hydroxyphenyl)-2-methylacrylate

3,4-dihydroxybenzaldehyde

3-hydroxy-4-(2-propenyloxy)benzaldehyde

Downstream raw materials:

(-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide

hygromycin A