ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-4-O-(methylsulfonyl)-α-D-talopyranoside

Base Information

• Chemical Name: ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-4-O-(methylsulfonyl)-α-D-talopyranoside
• CAS No.: 86646-61-9
• Molecular Formula: C₂₀H₂₈O₆S
• Molecular Weight: 396.505

Synonyms:ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-4-O-(methylsulfonyl)-α-D-talopyranoside

Chemical Property of ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-4-O-(methylsulfonyl)-α-D-talopyranoside

Chemical Property:

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Technology Process of ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-4-O-(methylsulfonyl)-α-D-talopyranoside

There total 5 articles about ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-4-O-(methylsulfonyl)-α-D-talopyranoside 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: 93.0%

methanesulfonyl chloride (124-63-0) + ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-α-D-talopyranoside (86646-60-8) → ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-4-O-(methylsulfonyl)-α-D-talopyranoside (86646-61-9)

Guidance literature:

In pyridine; for 7h; Ambient temperature;

DOI:10.1021/ja00356a026

Reference yield:

(2R)-2r-acetoxymethyl-6t-ethoxy-6H-pyran-3-one (25474-16-2) → ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-4-O-(methylsulfonyl)-α-D-talopyranoside (86646-61-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / AlCl₃ / CH₂Cl₂ / 2.5 h / -40 °C

2: 80 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

3: 67 percent / NaH / 1,2-dimethoxy-ethane / 4 h / Ambient temperature

4: 93 percent / pyridine / 7 h / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; sodium hydride; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/ja00356a026

Reference yield:

benzyl bromide (100-39-0) → ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-4-O-(methylsulfonyl)-α-D-talopyranoside (86646-61-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / NaH / 1,2-dimethoxy-ethane / 4 h / Ambient temperature

2: 93 percent / pyridine / 7 h / Ambient temperature

With sodium hydride; In pyridine; 1,2-dimethoxyethane;

DOI:10.1021/ja00356a026

upstream raw materials:

methanesulfonyl chloride

ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3-dideoxy-α-D-talopyranoside

(2R)-2r-acetoxymethyl-6t-ethoxy-6H-pyran-3-one

benzyl bromide

Downstream raw materials:

ethyl 6-O-benzyl-2,3-C-(2-butene-1,4-diyl)-2,3,4-trideoxy-β-L-erythro-hex-4-enopyranoside

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