2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester
• CAS No.: 322648-74-8
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386

Synonyms:2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester

There total 1 articles about 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl 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: 88.0%

pivaloyl chloride (3282-30-2) + 6-O-(benzyl)-D-glucal (165524-85-6) → 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester (322648-74-8)

Guidance literature:

With pyridine; dmap; In dichloromethane;

DOI:10.1021/ja0022730

Reference yield: 100.0%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester (322648-74-8) → C27H44O5Si

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ol8027225

Reference yield: 96.0%

triethylsilyl trifluoromethyl sulfonate (79271-56-0) + 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester (322648-74-8) → 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-triethylsilanyloxy-3,4-dihydro-2H-pyran-4-yl ester (322648-75-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/ja0022730

upstream raw materials:

pivaloyl chloride

6-O-(benzyl)-D-glucal

Downstream raw materials:

2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-triethylsilanyloxy-3,4-dihydro-2H-pyran-4-yl ester

6-O-benzyl-4-O-TES glucal

(3aS,4R,6R,7R,7aR)-4-Benzyloxymethyl-6-((2R,3S,4R)-2-benzyloxymethyl-3-triethylsilanyloxy-3,4-dihydro-2H-pyran-4-yloxy)-7-hydroxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

(3aS,4R,6R,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3S,4R)-2-benzyloxymethyl-3-triethylsilanyloxy-3,4-dihydro-2H-pyran-4-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

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