5-O-tert-butyldiphenylsilyl-3-deoxy-2,2'-O-isopropylidene-(2R,4S)-pentitol

Base Information

• Chemical Name: 5-O-tert-butyldiphenylsilyl-3-deoxy-2,2'-O-isopropylidene-(2R,4S)-pentitol
• CAS No.: 174272-26-5
• Molecular Formula: C₂₅H₃₆O₅Si
• Molecular Weight: 444.643

Synonyms:5-O-tert-butyldiphenylsilyl-3-deoxy-2,2'-O-isopropylidene-(2R,4S)-pentitol

Chemical Property of 5-O-tert-butyldiphenylsilyl-3-deoxy-2,2'-O-isopropylidene-(2R,4S)-pentitol

Chemical Property:

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Technology Process of 5-O-tert-butyldiphenylsilyl-3-deoxy-2,2'-O-isopropylidene-(2R,4S)-pentitol

There total 4 articles about 5-O-tert-butyldiphenylsilyl-3-deoxy-2,2'-O-isopropylidene-(2R,4S)-pentitol 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: 65.0%

5-O-tert-butyldiphenylsilyl-3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-erythro-pentono-1,4-lactone (174272-25-4) → 5-O-tert-butyldiphenylsilyl-3-deoxy-2,2'-O-isopropylidene-(2R,4S)-pentitol (174272-26-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(95)00264-2

Reference yield:

2,6-O-isopropylidene-α-D-glucoisosaccharino-1,4-lactone (78687-63-5) → 5-O-tert-butyldiphenylsilyl-3-deoxy-2,2'-O-isopropylidene-(2R,4S)-pentitol (174272-26-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

2: 65 percent / NaBH₄ / methanol / 2 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(95)00264-2

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 5-O-tert-butyldiphenylsilyl-3-deoxy-2,2'-O-isopropylidene-(2R,4S)-pentitol (174272-26-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

2: 65 percent / NaBH₄ / methanol / 2 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(95)00264-2

upstream raw materials:

5-O-tert-butyldiphenylsilyl-3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-erythro-pentono-1,4-lactone

2,6-O-isopropylidene-α-D-glucoisosaccharino-1,4-lactone

tert-butylchlorodiphenylsilane

3-deoxy-2-C-hydroxymethyl-D-erythro-pentono-1,4-lactone

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