(2S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzoyloxy-6-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzoyloxy-6-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester
• CAS No.: 138857-78-0
• Molecular Formula: C₂₅H₂₆O₁₀
• Molecular Weight: 486.475
• Mol file: 138857-78-0.mol

Synonyms:

Chemical Property of (2S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzoyloxy-6-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzoyloxy-6-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

There total 7 articles about (2S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzoyloxy-6-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl 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: 32.0%

pyruvic acid methyl ester (600-22-6) + C27H38O8Si2 (138857-62-2) → methyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranoside (129192-92-3) + (R)-4-((2S,3S,4R,5R)-3,4-Bis-benzoyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-methyl-[1,3]dioxolane-2-carboxylic acid methyl ester (138857-76-8,138857-77-9) + methyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-1-thio-α-D-galactopyranoside (138857-75-7) + (2S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzoyloxy-6-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (138857-78-0)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 20h; Further byproducts given. Title compound not separated from byproducts; Ambient temperature;

Reference yield: 8.0%

pyruvic acid methyl ester (600-22-6) + C32H40O8Si2 (138857-65-5) → methyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranoside (129192-92-3) + (R)-4-((2S,3S,4R,5R)-3,4-Bis-benzoyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-methyl-[1,3]dioxolane-2-carboxylic acid methyl ester (138857-76-8,138857-77-9) + (2S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzoyloxy-6-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (138857-78-0)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; Yield given. Yields of byproduct given. Title compound not separated from byproducts; 1.) -20 deg C, 2.) room temperature, 20 h;

Reference yield:

phenyl 4,6-O-benzylidene-β-D-galactopyranoside (42821-94-3) → (2S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzoyloxy-6-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (138857-78-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / pyridine / 2 h / Ambient temperature

2: 71 percent / 70percent aq. AcOH / 1 h / 90 °C

3: 91 percent / CF₃CO₂H / CH₂Cl₂ / 1.5 h / Ambient temperature

4: TMSOTf / CH₂Cl₂ / 1.) -20 deg C, 2.) room temperature, 20 h

With pyridine; acetic acid; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In dichloromethane;

upstream raw materials:

pyruvic acid methyl ester

C₂₇H₃₈O₈Si₂

C₃₂H₄₀O₈Si₂

phenyl 4,6-O-benzylidene-β-D-galactopyranoside