(2S,4aS,6R,8S,8aR)-6,8-Dimethoxy-7-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (2S,4aS,6R,8S,8aR)-6,8-Dimethoxy-7-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 148022-41-7
• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.332
• Mol file: 148022-41-7.mol

Synonyms:(2S,4aS,6R,8S,8aR)-6,8-Dimethoxy-7-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property of (2S,4aS,6R,8S,8aR)-6,8-Dimethoxy-7-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4aS,6R,8S,8aR)-6,8-Dimethoxy-7-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 2 articles about (2S,4aS,6R,8S,8aR)-6,8-Dimethoxy-7-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 75.0%

methyltriphenylphosphonium chloride (1031-15-8) + (2S,4aS,6R,8R,8aS)-6,8-Dimethoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one (148022-03-1) → (2S,4aS,6R,8S,8aR)-6,8-Dimethoxy-7-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (148022-41-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; -20 deg C to room temperature;

DOI:10.1016/S0040-4039(00)61633-7

Reference yield:

methyl 4,6-O-benzylidene-3-O-methyl-α-L-mannopyranoside → (2S,4aS,6R,8S,8aR)-6,8-Dimethoxy-7-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (148022-41-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (COCl)2, dimethylsulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C

2: 75 percent / n-BuLi / tetrahydrofuran / -20 deg C to room temperature

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)61633-7

Reference yield:

(2S,4aS,6R,8S,8aR)-6,8-Dimethoxy-7-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (148022-41-7) → (2S,3R,4S)-2-Benzyloxymethyl-4-methoxy-5-methylene-tetrahydro-pyran-3-ol

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; Yield given;

DOI:10.1016/S0040-4039(00)61633-7

upstream raw materials:

methyltriphenylphosphonium chloride

(2S,4aS,6R,8R,8aS)-6,8-Dimethoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one