Benzoic acid (2R,3R,4S,5S,6R)-2-fluoro-6-methyl-5-methylamino-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5S,6R)-2-fluoro-6-methyl-5-methylamino-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 358359-37-2
• Molecular Formula: C₂₅H₃₂FNO₁₁
• Molecular Weight: 541.528
• Mol file: 358359-37-2.mol

Synonyms:Benzoic acid (2R,3R,4S,5S,6R)-2-fluoro-6-methyl-5-methylamino-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3R,4S,5S,6R)-2-fluoro-6-methyl-5-methylamino-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3R,4S,5S,6R)-2-fluoro-6-methyl-5-methylamino-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

There total 4 articles about Benzoic acid (2R,3R,4S,5S,6R)-2-fluoro-6-methyl-5-methylamino-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 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: 78.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride (303153-45-9) → Benzoic acid (2R,3R,4S,5S,6R)-2-fluoro-6-methyl-5-methylamino-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (358359-37-2)

Guidance literature:

formaldehyd; 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride; With trimethylphosphane; In dichloromethane; for 13h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.166667h; Further stages.;

DOI:10.1002/chem.200700863

Reference yield:

4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride (303153-45-9) → Benzoic acid (2R,3R,4S,5S,6R)-2-fluoro-6-methyl-5-methylamino-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (358359-37-2)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂; toluene

2: CH₂Cl₂; toluene

3: NaBH₄

With sodium tetrahydroborate; In dichloromethane; toluene; 1: Staudinger reaction / 2: aza-Wittig reaction;

DOI:10.1055/s-2001-14646

Reference yield:

C27H37FNO11P → Benzoic acid (2R,3R,4S,5S,6R)-2-fluoro-6-methyl-5-methylamino-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (358359-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂; toluene

2: NaBH₄

With sodium tetrahydroborate; In dichloromethane; toluene; 1: aza-Wittig reaction;

DOI:10.1055/s-2001-14646

upstream raw materials:

4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride

formaldehyd