6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal

Base Information

• Chemical Name: 6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal
• CAS No.: 1033614-33-3
• Molecular Formula: C₂₆H₄₀O₉SSi
• Molecular Weight: 556.75

Synonyms:6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal

Chemical Property of 6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal

Chemical Property:

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Technology Process of 6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal

There total 1 articles about 6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal 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: 72.0%

3-O-(t-butyldimethylsilyl)-4-O-mesyl-D-glucal (1033614-31-1) + 6-O-(benzyl)-4-O-mesyl-D-glucal (557793-03-0) → 6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal (1033614-33-3)

Guidance literature:

6-O-(benzyl)-4-O-mesyl-D-glucal; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.333333h; Inert atmosphere;

3-O-(t-butyldimethylsilyl)-4-O-mesyl-D-glucal; In tetrahydrofuran; at 20 ℃; for 18h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol800793f

Reference yield:

6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal (1033614-33-3) → 6-O-[6'-O-(benzyl)-2',3'-dideoxy-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-D-glucal (1033614-52-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol800793f

Reference yield:

6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal (1033614-33-3) + acetic anhydride (108-24-7) → 6-O-[6'-O-(benzyl)-4'-O-acetyl-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal (1033614-36-6)

Guidance literature:

With pyridine; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol800793f

upstream raw materials:

3-O-(t-butyldimethylsilyl)-4-O-mesyl-D-glucal

6-O-(benzyl)-4-O-mesyl-D-glucal

Downstream raw materials:

6-O-[6'-O-(benzyl)-2',3'-dideoxy-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-D-glucal

6-O-[6'-O-(benzyl)-4'-O-acetyl-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal

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