1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-hydroxyethoxy)cyclohexanol

Base Information

• Chemical Name: 1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-hydroxyethoxy)cyclohexanol
• CAS No.: 915193-62-3
• Molecular Formula: C₂₈H₄₃NO₁₅
• Molecular Weight: 633.647
• Mol file: 915193-62-3.mol

Synonyms:1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-hydroxyethoxy)cyclohexanol

Chemical Property of 1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-hydroxyethoxy)cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-hydroxyethoxy)cyclohexanol

There total 4 articles about 1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-hydroxyethoxy)cyclohexanol 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: 91.0%

1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-dioxolanylcyclohexanol (915193-61-2) → 1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-hydroxyethoxy)cyclohexanol (915193-62-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; In dichloromethane; at -78 ℃; for 4h;

DOI:10.1002/anie.200601209

Reference yield:

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (6931-68-6,72690-21-2,74006-95-4,108740-37-0,108740-38-1,108740-39-2,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,73208-82-9) → 1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-hydroxyethoxy)cyclohexanol (915193-62-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / SmI₂ / tetrahydrofuran / 2 h / 20 °C

2: 91 percent / trimethylsilyl trifluoromethanesulfonate; BH₃*Me₂S / CH₂Cl₂ / 4 h / -78 °C

With samarium diiodide; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.200700181

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → 1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-hydroxyethoxy)cyclohexanol (915193-62-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / SmI₂ / tetrahydrofuran / 2 h / 20 °C

2: 91 percent / TMSOTf; BH₃*SMe₂ / CH₂Cl₂ / 4 h / -78 °C

With samarium diiodide; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane; 1: Reformatsky reaction;

DOI:10.1002/anie.200601209

upstream raw materials:

1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-dioxolanylcyclohexanol

cyclohexanedione monoethylene ketal

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Downstream raw materials:

1-C-(methyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-allyloxyethoxy)cyclohexanol

1-C-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonate)-4-(2'-allyloxyethoxy)cyclohexanol