methyl (2R,4aR,6S,9aR,9bS)-4,4a,6,8,9a,9b-hexahydro-6-methoxy-8-oxo-2-phenylfuro[2',3':4,5]pyrano[3,2-d]-1,3-dioxin-7-carboxylate

Base Information

• Chemical Name: methyl (2R,4aR,6S,9aR,9bS)-4,4a,6,8,9a,9b-hexahydro-6-methoxy-8-oxo-2-phenylfuro[2',3':4,5]pyrano[3,2-d]-1,3-dioxin-7-carboxylate
• CAS No.: 382591-40-4
• Molecular Formula: C₁₈H₁₈O₈
• Molecular Weight: 362.336

Synonyms:methyl (2R,4aR,6S,9aR,9bS)-4,4a,6,8,9a,9b-hexahydro-6-methoxy-8-oxo-2-phenylfuro[2',3':4,5]pyrano[3,2-d]-1,3-dioxin-7-carboxylate

Chemical Property of methyl (2R,4aR,6S,9aR,9bS)-4,4a,6,8,9a,9b-hexahydro-6-methoxy-8-oxo-2-phenylfuro[2',3':4,5]pyrano[3,2-d]-1,3-dioxin-7-carboxylate

Chemical Property:

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Technology Process of methyl (2R,4aR,6S,9aR,9bS)-4,4a,6,8,9a,9b-hexahydro-6-methoxy-8-oxo-2-phenylfuro[2',3':4,5]pyrano[3,2-d]-1,3-dioxin-7-carboxylate

There total 3 articles about methyl (2R,4aR,6S,9aR,9bS)-4,4a,6,8,9a,9b-hexahydro-6-methoxy-8-oxo-2-phenylfuro[2',3':4,5]pyrano[3,2-d]-1,3-dioxin-7-carboxylate 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: 68.0%

methyl 4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose (126924-10-5) + diethyl malonate (105-53-3) → methyl (2R,4aR,6S,9aR,9bS)-4,4a,6,8,9a,9b-hexahydro-6-methoxy-8-oxo-2-phenylfuro[2',3':4,5]pyrano[3,2-d]-1,3-dioxin-7-carboxylate (382591-40-4)

Guidance literature:

diethyl malonate; With sodium; In methanol; at 0 ℃; for 0.166667h;

methyl 4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose; In methanol; chloroform; for 0.5h;

DOI:10.1016/S0008-6215(03)00257-X

Reference yield:

malonic acid dimethyl ester (108-59-8) + methyl 4,6-O-benzylidene-α-D-2-ketoglucopyranoside → methyl (2R,4aR,6S,9aR,9bS)-4,4a,6,8,9a,9b-hexahydro-6-methoxy-8-oxo-2-phenylfuro[2',3':4,5]pyrano[3,2-d]-1,3-dioxin-7-carboxylate (382591-40-4)

Guidance literature:

With sodium methylate; In chloroform;

DOI:10.1107/S0108270101015505

Reference yield:

diethyl malonate (105-53-3) + methyl 4,6-O-benzylidene-α-D-2-ketoglucopyranoside → methyl (2R,4aR,6S,9aR,9bS)-4,4a,6,8,9a,9b-hexahydro-6-methoxy-8-oxo-2-phenylfuro[2',3':4,5]pyrano[3,2-d]-1,3-dioxin-7-carboxylate (382591-40-4)

Guidance literature:

With sodium methylate; In chloroform;

DOI:10.1107/S0108270101015505

upstream raw materials:

malonic acid dimethyl ester

diethyl malonate

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

Downstream raw materials:

(E)-methyl 4-[hydroxy(methoxy)methylene]-5-oxo-1-propyl-(4,6-O-benzylidene-2-deoxy-α-D-glucopyranosido)[3,2-b]pyrrolidine

(E)-methyl 4-[hydroxy(methoxy)methylene]-5-oxo-1-(3-methylbutyl)-(4,6-O-benzylidene-2-deoxy-α-D-glucopyranosido)[3,2-b]pyrrolidine

(E)-methyl 4-[hydroxy(methoxy)methylene]-5-oxo-1-cyclohexyl-(4,6-O-benzylidene-2-deoxy-α-D-glucopyranosido)[3,2-b]pyrrolidine

(E)-methyl 4-[hydroxy(methoxy)methylene]-5-oxo-1-butyl-(4,6-O-benzylidene-2-deoxy-α-D-glucopyranosido)[3,2-b]pyrrolidine

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