5-(4-methoxybenzyloxymethyl)-2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydrodi-1,3-dioxolo[4,5-b:4',5'-d]pyran

Base Information

• Chemical Name: 5-(4-methoxybenzyloxymethyl)-2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydrodi-1,3-dioxolo[4,5-b:4',5'-d]pyran
• CAS No.: 218937-73-6
• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.438

Synonyms:5-(4-methoxybenzyloxymethyl)-2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydrodi-1,3-dioxolo[4,5-b:4',5'-d]pyran

Chemical Property of 5-(4-methoxybenzyloxymethyl)-2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydrodi-1,3-dioxolo[4,5-b:4',5'-d]pyran

Chemical Property:

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Technology Process of 5-(4-methoxybenzyloxymethyl)-2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydrodi-1,3-dioxolo[4,5-b:4',5'-d]pyran

There total 8 articles about 5-(4-methoxybenzyloxymethyl)-2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydrodi-1,3-dioxolo[4,5-b:4',5'-d]pyran 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: 97.0%

methanol (67-56-1) + 6-O-(4-chlorobenzyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside (294637-30-2) → 5-(4-methoxybenzyloxymethyl)-2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydrodi-1,3-dioxolo[4,5-b:4',5'-d]pyran (218937-73-6)

Guidance literature:

With di-tert-butyl (2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1‘-biphenyl]-2-yl)phosphine; methanesulfonato(2-(di-tert-butylphosphino)-3-methoxy-6-methyl-2′,4′,6′-tri-isopropyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)palladium(II); sodium t-butanolate; In 1,4-dioxane; at 50 ℃; for 20.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02672

Reference yield: 91.0%

p-Methoxybenzyl bromide (2746-25-0) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → 5-(4-methoxybenzyloxymethyl)-2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydrodi-1,3-dioxolo[4,5-b:4',5'-d]pyran (218937-73-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1021/jo026897v

Reference yield: 85.0%

4-Methoxybenzyl alcohol (105-13-5) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → 5-(4-methoxybenzyloxymethyl)-2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydrodi-1,3-dioxolo[4,5-b:4',5'-d]pyran (218937-73-6)

Guidance literature:

With ytterbium(III) triflate; In dichloromethane; at 20 ℃; for 28h;

DOI:10.1021/jo990563x

upstream raw materials:

4-methoxybenzyl-2-pyridylthio carbonate

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

4-Methoxybenzyl alcohol

p-Methoxybenzyl bromide

Downstream raw materials:

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

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