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

Base Information

• Chemical Name: (4aR,6S,7R,8R,8aS)-7,8-Dihydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester
• CAS No.: 553663-01-7
• Molecular Formula: C₁₆H₂₀O₈
• Molecular Weight: 340.33
• Mol file: 553663-01-7.mol

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

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

There total 1 articles about (4aR,6S,7R,8R,8aS)-7,8-Dihydroxy-6-methoxy-2-phenyl-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: 76.0%

methyl acetyl of methyl phenylglyoxylate (85810-81-7) + methyl-alpha-D-glucopyranoside (97-30-3) → (4aR,6S,7R,8R,8aS)-7,8-Dihydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (553663-01-7)

Guidance literature:

With camphor-10-sulfonic acid; In acetonitrile; Heating;

DOI:10.1021/ol034741r

Reference yield:

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (4aR,6S,7R,8R,8aS)-7,8-Dihydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (553663-01-7) → (4aR,6S,7R,8S,8aR)-6-Methoxy-2-phenyl-7,8-bis-trimethylsilanyloxy-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (553663-02-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol034741r

Reference yield:

(4aR,6S,7R,8R,8aS)-7,8-Dihydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (553663-01-7) → Acetic acid (2S,4aR,6S,7R,8S,8aR)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (553663-03-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

2: 90 percent / AlMe₃ / hexane; toluene / 5 h / Heating

3: TBAF / CH₂Cl₂; hexane / 1 h / 20 °C

4: 347 mg / pyridine; DMAP / 3 h

With pyridine; dmap; tetrabutyl ammonium fluoride; trimethylaluminum; triethylamine; In hexane; dichloromethane; toluene;

DOI:10.1021/ol034741r

upstream raw materials:

methyl acetyl of methyl phenylglyoxylate

methyl-alpha-D-glucopyranoside

Downstream raw materials:

(4aR,6S,7R,8S,8aR)-6-Methoxy-2-phenyl-7,8-bis-trimethylsilanyloxy-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Benzoic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Acetic acid (2S,4aR,6S,7R,8S,8aR)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester