8'-phthalimidooctyl 5-deoxy-5-(E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl)-thio-α-L-arabinofuranoside

Base Information

Chemical Name:8'-phthalimidooctyl 5-deoxy-5-(E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl)-thio-α-L-arabinofuranoside
CAS No.:290820-44-9
Molecular Formula:C₃₇H₅₃NO₈SSi
Molecular Weight:699.981
Hs Code.:

Synonyms:8'-phthalimidooctyl 5-deoxy-5-(E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl)-thio-α-L-arabinofuranoside

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Chemical Property of 8'-phthalimidooctyl 5-deoxy-5-(E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl)-thio-α-L-arabinofuranoside

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Technology Process of 8'-phthalimidooctyl 5-deoxy-5-(E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl)-thio-α-L-arabinofuranoside

There total 12 articles about 8'-phthalimidooctyl 5-deoxy-5-(E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl)-thio-α-L-arabinofuranoside 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: 27.0%

: 290820-43-8
E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl thiol

: 290820-42-7
8'-phthalimidooctyl 5-O-(p-toluenesulfonyl)-α-L-arabinofuranoside

: 290820-44-9
8'-phthalimidooctyl 5-deoxy-5-(E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl)-thio-α-L-arabinofuranoside

Guidance literature:: E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl thiol; With sodium ethanolate; In ethanol; for 2h;

8'-phthalimidooctyl 5-O-(p-toluenesulfonyl)-α-L-arabinofuranoside; In ethanol; for 18h; Heating;
DOI:10.1016/S0968-0896(00)00037-7

Reference yield:

: 42868-96-2
2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide

: 290820-44-9
8'-phthalimidooctyl 5-deoxy-5-(E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl)-thio-α-L-arabinofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 60.6 percent / Hg(CN)2; Na₂CO₃ / tetrahydrofuran / 24 h / 20 °C

2.1: 81 percent / NaOMe / methanol

3.1: 77.7 percent / pyridine / 0 - 20 °C

4.1: NaOEt / ethanol / 2 h

4.2: 27 percent / ethanol / 18 h / Heating

With pyridine; sodium methylate; sodium ethanolate; mercury(II) cyanide; sodium carbonate; In tetrahydrofuran; methanol; ethanol; 1.1: Substitution / 2.1: debenzoylation / 3.1: Tosylation / 4.1: deprotonation / 4.2: Substitution;
DOI:10.1016/S0968-0896(00)00037-7

Reference yield:

: 50816-19-8
8-bromooctanol

: 290820-44-9
8'-phthalimidooctyl 5-deoxy-5-(E-4-O-(tert-butyldimethylsilyl)-3-methoxycinnamyl)-thio-α-L-arabinofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / dimethylformamide / 0.5 h / 90 °C

2.1: 60.6 percent / Hg(CN)2; Na₂CO₃ / tetrahydrofuran / 24 h / 20 °C

3.1: 81 percent / NaOMe / methanol

4.1: 77.7 percent / pyridine / 0 - 20 °C

5.1: NaOEt / ethanol / 2 h

5.2: 27 percent / ethanol / 18 h / Heating

With pyridine; sodium methylate; sodium ethanolate; mercury(II) cyanide; sodium carbonate; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Substitution / 3.1: debenzoylation / 4.1: Tosylation / 5.1: deprotonation / 5.2: Substitution;
DOI:10.1016/S0968-0896(00)00037-7