5-S-acetyl-3-C-<2'-O-(tert-butyldiphenylsilyloxy)ethyl>-3,5-dideoxy-1,2-O-isopropylidene-5-thio-α-D-ribofuranose

Base Information

Chemical Name:5-S-acetyl-3-C-<2'-O-(tert-butyldiphenylsilyloxy)ethyl>-3,5-dideoxy-1,2-O-isopropylidene-5-thio-α-D-ribofuranose
CAS No.:134353-80-3
Molecular Formula:C₂₈H₃₈O₅SSi
Molecular Weight:514.758
Hs Code.:

Synonyms:5-S-acetyl-3-C-<2'-O-(tert-butyldiphenylsilyloxy)ethyl>-3,5-dideoxy-1,2-O-isopropylidene-5-thio-α-D-ribofuranose

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Chemical Property of 5-S-acetyl-3-C-<2'-O-(tert-butyldiphenylsilyloxy)ethyl>-3,5-dideoxy-1,2-O-isopropylidene-5-thio-α-D-ribofuranose

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Technology Process of 5-S-acetyl-3-C-<2'-O-(tert-butyldiphenylsilyloxy)ethyl>-3,5-dideoxy-1,2-O-isopropylidene-5-thio-α-D-ribofuranose

There total 4 articles about 5-S-acetyl-3-C-<2'-O-(tert-butyldiphenylsilyloxy)ethyl>-3,5-dideoxy-1,2-O-isopropylidene-5-thio-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%

: 133508-14-2
3-C-<2'-O-(tert-butyldiphenylsilyloxy)ethyl>-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

: 507-09-5
tiolacetic acid

: 134353-80-3
5-S-acetyl-3-C-<2'-O-(tert-butyldiphenylsilyloxy)ethyl>-3,5-dideoxy-1,2-O-isopropylidene-5-thio-α-D-ribofuranose

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran;
DOI:10.1016/0008-6215(91)80095-5

Reference yield:

: 20590-54-9
1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose

: 134353-80-3
5-S-acetyl-3-C-<2'-O-(tert-butyldiphenylsilyloxy)ethyl>-3,5-dideoxy-1,2-O-isopropylidene-5-thio-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: 1) NaH, 3) LiAlH₄

2: 98 percent / imidazole / dimethylformamide / Ambient temperature

3: 92 percent / trichloroacetic acid / CH₂Cl₂ / Ambient temperature

4: 84 percent / diisopropyl azodicarboxylate, triphenylphosphine / tetrahydrofuran

With 1H-imidazole; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; sodium hydride; triphenylphosphine; trichloroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(91)80095-5

Reference yield:

: 58399-76-1
3-Deoxy-3-C-(2'-hydroxyethyl)-1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-ribofuranose

: 134353-80-3
5-S-acetyl-3-C-<2'-O-(tert-butyldiphenylsilyloxy)ethyl>-3,5-dideoxy-1,2-O-isopropylidene-5-thio-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / imidazole / dimethylformamide / Ambient temperature

2: 92 percent / trichloroacetic acid / CH₂Cl₂ / Ambient temperature

3: 84 percent / diisopropyl azodicarboxylate, triphenylphosphine / tetrahydrofuran

With 1H-imidazole; di-isopropyl azodicarboxylate; triphenylphosphine; trichloroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(91)80095-5