Acetic acid (2S,3R,4S,5S)-2-acetoxy-5-acetylsulfanylmethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3R,4S,5S)-2-acetoxy-5-acetylsulfanylmethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-3-yl ester
CAS No.:134353-81-4
Molecular Formula:C₂₉H₃₈O₇SSi
Molecular Weight:558.768
Hs Code.:

Synonyms:Acetic acid (2S,3R,4S,5S)-2-acetoxy-5-acetylsulfanylmethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-3-yl ester

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Chemical Property of Acetic acid (2S,3R,4S,5S)-2-acetoxy-5-acetylsulfanylmethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5S)-2-acetoxy-5-acetylsulfanylmethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-3-yl ester

There total 6 articles about Acetic acid (2S,3R,4S,5S)-2-acetoxy-5-acetylsulfanylmethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-3-yl ester 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: 80.0%

: 108-24-7
acetic anhydride

: 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

: 134353-81-4
Acetic acid (2S,3R,4S,5S)-2-acetoxy-5-acetylsulfanylmethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-3-yl ester

Guidance literature:: With camphor-10-sulfonic acid; In acetic acid; at 75 ℃; for 0.25h;
DOI:10.1016/0008-6215(91)80095-5

Reference yield: 8.0%

: 108-24-7
acetic anhydride

: 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

: 134353-81-4
Acetic acid (2S,3R,4S,5S)-2-acetoxy-5-acetylsulfanylmethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-3-yl ester

: 134353-82-5,134353-83-6
Acetic acid (1S,2S)-2-((4R,5S)-5-acetoxy-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-acetylsulfanylmethyl-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

: 134353-82-5,134353-83-6
Acetic acid (1S,2S)-2-((4R,5R)-5-acetoxy-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-acetylsulfanylmethyl-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Guidance literature:: With camphor-10-sulfonic acid; In acetic acid; at 15 ℃; for 24h;
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

: 134353-81-4
Acetic acid (2S,3R,4S,5S)-2-acetoxy-5-acetylsulfanylmethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 5 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

5: 80 percent / (+/-)- camphorsulfonic acid / acetic acid / 0.25 h / 75 °C

With 1H-imidazole; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; sodium hydride; triphenylphosphine; trichloroacetic acid; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(91)80095-5