methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose
• CAS No.: 88390-61-8
• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.304
• Mol file: 88390-61-8.mol

Synonyms:methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose

Chemical Property of methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose

There total 3 articles about methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose 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: 70.0%

methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-arabinohexopyranosid-3-ulose (88390-62-9) → methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose (88390-61-8)

Guidance literature:

With triethylamine; In ethanol; for 5h; Reflux;

DOI:10.1016/j.tet.2011.07.014

Reference yield:

methyl 4,6-O-benzylidene-2-O-methyl-α-D-glucopyranoside (110715-29-2) + (2R,4aR,6S,7R,8R,8aR)-6,8-dimethoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol (93302-38-6) → methyl 4,6-O-benzylidene-3-O-methyl-α-D-arabino-hexopyranosid-2-ulosee (74410-54-1) + methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose (88390-61-8)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2009.08.080

Reference yield:

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside (66537-92-6) → methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose (88390-61-8)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol / Reflux

2: pyridinium chlorochromate / dichloromethane / 20 °C / Molecular sieve

3: triethylamine / ethanol / 5 h / Reflux

With triethylamine; pyridinium chlorochromate; In methanol; ethanol; dichloromethane;

DOI:10.1016/j.tet.2011.07.014

upstream raw materials:

methyl 4,6-O-benzylidene-2-O-methyl-α-D-glucopyranoside

(2R,4aR,6S,7R,8R,8aR)-6,8-dimethoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol

methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-arabinohexopyranosid-3-ulose

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside

Downstream raw materials:

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

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

(2R,4aR,6S,7R,8aS)-8-[1-Chloro-meth-(E)-ylidene]-6,7-dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

C₁₆H₁₉ClO₆