2-((2R,4aR,6R,7S,8R,8aR)-8-Benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-((2R,4aR,6R,7S,8R,8aR)-8-Benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-malonic acid dimethyl ester
• CAS No.: 526197-24-0
• Molecular Formula: C₂₅H₂₈O₁₀S
• Molecular Weight: 520.557
• Mol file: 526197-24-0.mol

Synonyms:2-((2R,4aR,6R,7S,8R,8aR)-8-Benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-malonic acid dimethyl ester

Chemical Property of 2-((2R,4aR,6R,7S,8R,8aR)-8-Benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2R,4aR,6R,7S,8R,8aR)-8-Benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-malonic acid dimethyl ester

There total 1 articles about 2-((2R,4aR,6R,7S,8R,8aR)-8-Benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-malonic acid dimethyl 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: 98.0%

malonic acid dimethyl ester (108-59-8) + methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside (273921-08-7) → 2-((2R,4aR,6R,7S,8R,8aR)-8-Benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-malonic acid dimethyl ester (526197-24-0)

Guidance literature:

malonic acid dimethyl ester; With sodium hydride; In tetrahydrofuran;

methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ol0342047

Reference yield: 84.0%

2-((2R,4aR,6R,7S,8R,8aR)-8-Benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-malonic acid dimethyl ester (526197-24-0) → 2-((2R,3S,4R,5R,6R)-4-Benzenesulfonyl-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-malonic acid dimethyl ester (526197-29-5)

Guidance literature:

With hydrogenchloride; In ethanol; at 20 ℃; for 2.5h;

DOI:10.1021/ol0342047

Reference yield:

2-((2R,4aR,6R,7S,8R,8aR)-8-Benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-malonic acid dimethyl ester (526197-24-0) → 2-((2R,3S,6S)-4-Benzenesulfonyl-6-methanesulfonyloxymethyl-2-methoxy-3,6-dihydro-2H-pyran-3-yl)-malonic acid dimethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / aq. HCl / ethanol / 2.5 h / 20 °C

2: 92 percent / pyridine / 24 h / 0 - 4 °C

With pyridine; hydrogenchloride; In ethanol;

DOI:10.1021/ol0342047

upstream raw materials:

malonic acid dimethyl ester

methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside

Downstream raw materials:

2-((2R,3S,4R,5R,6R)-4-Benzenesulfonyl-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-malonic acid dimethyl ester