methyl [2-(trimethylsilyl)ethyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate

Base Information

• Chemical Name: methyl [2-(trimethylsilyl)ethyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
• CAS No.: 361192-55-4
• Molecular Formula: C₂₈H₄₀F₃NO₁₁Si
• Molecular Weight: 651.706
• Mol file: 361192-55-4.mol

Synonyms:methyl [2-(trimethylsilyl)ethyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate

Chemical Property of methyl [2-(trimethylsilyl)ethyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [2-(trimethylsilyl)ethyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate

There total 5 articles about methyl [2-(trimethylsilyl)ethyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 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: 72.0%

(2R,4S,5R,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2-phenyl-[1,3]dioxolan-4-yl)-methyl]-5-(2,2,2-trifluoro-acetylamino)-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (361192-52-1) → methyl [2-(trimethylsilyl)ethyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate (361192-55-4)

Guidance literature:

With aluminium trichloride; dimethylamine borane; 4 A molecular sieve; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo010345f

Reference yield:

methyl [2-(trimethylsilyl)ethyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α,β-D-galacto-non-2-ulopyranosid]onate → methyl [2-(trimethylsilyl)ethyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate (361192-55-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / NaOMe / methanol / 2 h

2: 61 percent / CSA / acetonitrile / 1 h

3: 96 percent / pyridine / 16 h

4: 72 percent / BH₃*NMe₂; AlCl₃; molecular sieves 4 Angstroem / tetrahydrofuran / 0 - 20 °C

With pyridine; aluminium trichloride; dimethylamine borane; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jo010345f

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → methyl [2-(trimethylsilyl)ethyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate (361192-55-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / CSA / acetonitrile / 1 h

2: 96 percent / pyridine / 16 h

3: 72 percent / BH₃*NMe₂; AlCl₃; molecular sieves 4 Angstroem / tetrahydrofuran / 0 - 20 °C

With pyridine; aluminium trichloride; dimethylamine borane; 4 A molecular sieve; camphor-10-sulfonic acid; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo010345f

upstream raw materials:

(2R,4S,5R,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2-phenyl-[1,3]dioxolan-4-yl)-methyl]-5-(2,2,2-trifluoro-acetylamino)-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

benzaldehyde dimethyl acetal

methyl [2-(trimethylsilyl)ethyl 3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate

methyl [2-(trimethylsilyl)ethyl 8,9-O-benzylidene-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate

Downstream raw materials:

C₄₈H₆₄F₆N₂O₂₃Si

methyl [2,4,7-tri-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate

methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate