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

Base Information

• Chemical Name: 5-O-tert-butyldiphenylsilyl-3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-erythro-pentono-1,4-lactone
• CAS No.: 174272-25-4
• Molecular Formula: C₂₅H₃₂O₅Si
• Molecular Weight: 440.612

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

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

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

There total 2 articles about 5-O-tert-butyldiphenylsilyl-3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-erythro-pentono-1,4-lactone 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: 58.0%

2,6-O-isopropylidene-α-D-glucoisosaccharino-1,4-lactone (78687-63-5) + tert-butylchlorodiphenylsilane (58479-61-1) → 5-O-tert-butyldiphenylsilyl-3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-erythro-pentono-1,4-lactone (174272-25-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 15h; Ambient temperature;

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

Reference yield:

3-deoxy-2-C-hydroxymethyl-D-erythro-pentono-1,4-lactone (7397-89-9) → 5-O-tert-butyldiphenylsilyl-3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-erythro-pentono-1,4-lactone (174272-25-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / conc. H₂SO₄, CuSO₄ / 3 h / Ambient temperature

2: 58 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

With 1H-imidazole; sulfuric acid; copper(II) sulfate; In N,N-dimethyl-formamide;

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

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

upstream raw materials:

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

tert-butylchlorodiphenylsilane

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

Downstream raw materials:

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

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