(3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate
• CAS No.: 78785-03-2
• Molecular Formula: C₁₆H₂₀O₇S
• Molecular Weight: 356.397

Synonyms:(3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate

Chemical Property of (3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate

Chemical Property:

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Technology Process of (3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate

There total 2 articles about (3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate 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: 85.0%

6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose (78785-02-1) → (3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate (78785-03-2)

Guidance literature:

With sodium acetate; pyridinium chlorochromate;

DOI:10.1002/cber.19811140605

Reference yield:

1,2-O-Isopropyliden-3,6-bis-O-(4-methylphenylsulfonyl)-α-D-glucofuranose (16848-25-2) → (3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate (78785-03-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / LiAlH₄ / tetrahydrofuran / Heating

2: 85 percent / pyridinium chlorochromate, NaOAc

With lithium aluminium tetrahydride; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran;

DOI:10.1002/cber.19811140605

Reference yield: 85.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate (78785-03-2) → (3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate (78785-04-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -10 - 0 ℃;

DOI:10.1002/cber.19811140605

upstream raw materials:

6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose

1,2-O-Isopropyliden-3,6-bis-O-(4-methylphenylsulfonyl)-α-D-glucofuranose

Downstream raw materials:

(3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate

Methyl-6-O-benzyl-3,5-didesoxy-5-C-methyl-L-lyxo-hexofuranosid

Toluene-4-sulfonic acid (2R,3R,4R)-4,5-dihydroxy-2-((R)-2-hydroxy-1-methyl-ethyl)-tetrahydro-furan-3-yl ester

Methyl-6-O-benzyl-5-desoxy-5-C-methyl-3-O-(4-methylphenylsulfonyl)-L-idofuranosid

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