5-O-(tert-butyldiphenylsilyl)-1'-(benzenesulfonylmethylene)-2',3'-O-isopropylidene-α-D-ribofuranose

Base Information

• Chemical Name: 5-O-(tert-butyldiphenylsilyl)-1'-(benzenesulfonylmethylene)-2',3'-O-isopropylidene-α-D-ribofuranose
• CAS No.: 582312-81-0
• Molecular Formula: C₃₁H₃₈O₇SSi
• Molecular Weight: 582.79

Synonyms:5-O-(tert-butyldiphenylsilyl)-1'-(benzenesulfonylmethylene)-2',3'-O-isopropylidene-α-D-ribofuranose

Chemical Property of 5-O-(tert-butyldiphenylsilyl)-1'-(benzenesulfonylmethylene)-2',3'-O-isopropylidene-α-D-ribofuranose

Chemical Property:

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Technology Process of 5-O-(tert-butyldiphenylsilyl)-1'-(benzenesulfonylmethylene)-2',3'-O-isopropylidene-α-D-ribofuranose

There total 3 articles about 5-O-(tert-butyldiphenylsilyl)-1'-(benzenesulfonylmethylene)-2',3'-O-isopropylidene-α-D-ribofuranose 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: 84.0%

methylphenylsulfonate (3112-85-4) + 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3) → 5-O-(tert-butyldiphenylsilyl)-1'-(benzenesulfonylmethylene)-2',3'-O-isopropylidene-α-D-ribofuranose (582312-81-0)

Guidance literature:

methylphenylsulfonate; With n-butyllithium; In tetrahydrofuran; at -60 - -10 ℃;

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone; In tetrahydrofuran; at -60 - -35 ℃;

DOI:10.1002/jhet.5570400218

Reference yield:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → 5-O-(tert-butyldiphenylsilyl)-1'-(benzenesulfonylmethylene)-2',3'-O-isopropylidene-α-D-ribofuranose (582312-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: nBuLi / tetrahydrofuran / -60 - -10 °C

2.2: 84 percent / tetrahydrofuran / -60 - -35 °C

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570400218

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 5-O-(tert-butyldiphenylsilyl)-1'-(benzenesulfonylmethylene)-2',3'-O-isopropylidene-α-D-ribofuranose (582312-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: nBuLi / tetrahydrofuran / -60 - -10 °C

2.2: 84 percent / tetrahydrofuran / -60 - -35 °C

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570400218

upstream raw materials:

methylphenylsulfonate

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

2,3-O-isopropylidene-D-ribonic-γ-lactone

tert-butylchlorodiphenylsilane

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