3-C<(1R)-1-acetoxy-2-O-(tert-butyldiphenylsilyloxy)>-1,2-di-O-acetyl-3,4,5-trideoxy-5-thio-β-L-threo-pentopyranose

Base Information

Chemical Name:3-C<(1R)-1-acetoxy-2-O-(tert-butyldiphenylsilyloxy)>-1,2-di-O-acetyl-3,4,5-trideoxy-5-thio-β-L-threo-pentopyranose
CAS No.:134353-79-0
Molecular Formula:C₂₉H₃₈O₇SSi
Molecular Weight:558.768
Hs Code.:

Synonyms:3-C<(1R)-1-acetoxy-2-O-(tert-butyldiphenylsilyloxy)>-1,2-di-O-acetyl-3,4,5-trideoxy-5-thio-β-L-threo-pentopyranose

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Chemical Property of 3-C<(1R)-1-acetoxy-2-O-(tert-butyldiphenylsilyloxy)>-1,2-di-O-acetyl-3,4,5-trideoxy-5-thio-β-L-threo-pentopyranose

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Technology Process of 3-C<(1R)-1-acetoxy-2-O-(tert-butyldiphenylsilyloxy)>-1,2-di-O-acetyl-3,4,5-trideoxy-5-thio-β-L-threo-pentopyranose

There total 5 articles about 3-C<(1R)-1-acetoxy-2-O-(tert-butyldiphenylsilyloxy)>-1,2-di-O-acetyl-3,4,5-trideoxy-5-thio-β-L-threo-pentopyranose 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: 70.0%

: 108-24-7
acetic anhydride

: 134353-77-8
3-C-<2'-(acetylthio)ethyl>-5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

: 134353-79-0
3-C<(1R)-1-acetoxy-2-O-(tert-butyldiphenylsilyloxy)>-1,2-di-O-acetyl-3,4,5-trideoxy-5-thio-β-L-threo-pentopyranose

Guidance literature:: With boron trifluoride diethyl etherate; at 0 ℃;
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

: 134353-79-0
3-C<(1R)-1-acetoxy-2-O-(tert-butyldiphenylsilyloxy)>-1,2-di-O-acetyl-3,4,5-trideoxy-5-thio-β-L-threo-pentopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 1) NaH, 3) LiAlH₄

2: diisopropyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 1.) 30 min, 0 deg C, 2.) to r.t., 1 h

3: 78 percent / trichloroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

4: 99 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

5: 70 percent / BF₃OEt₂ / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; 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

: 134353-79-0
3-C<(1R)-1-acetoxy-2-O-(tert-butyldiphenylsilyloxy)>-1,2-di-O-acetyl-3,4,5-trideoxy-5-thio-β-L-threo-pentopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: diisopropyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 1.) 30 min, 0 deg C, 2.) to r.t., 1 h

2: 78 percent / trichloroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

3: 99 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

4: 70 percent / BF₃OEt₂ / 0 °C

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