N-tertbutyloxycarbonyl-trans-4-O-(3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl)oxy-L-proline benzyl ester

Base Information

Chemical Name:N-tertbutyloxycarbonyl-trans-4-O-(3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl)oxy-L-proline benzyl ester
CAS No.:1451369-70-2
Molecular Formula:C₃₄H₅₇NO₁₀Si₂
Molecular Weight:695.998
Hs Code.:

Synonyms:N-tertbutyloxycarbonyl-trans-4-O-(3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl)oxy-L-proline benzyl ester

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Chemical Property of N-tertbutyloxycarbonyl-trans-4-O-(3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl)oxy-L-proline benzyl ester

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Technology Process of N-tertbutyloxycarbonyl-trans-4-O-(3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl)oxy-L-proline benzyl ester

There total 4 articles about N-tertbutyloxycarbonyl-trans-4-O-(3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl)oxy-L-proline benzyl 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: 67.0%

: 1451369-96-2
C₅₂H₇₁NO₁₀SSi₂

: 1451369-70-2
N-tertbutyloxycarbonyl-trans-4-O-(3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl)oxy-L-proline benzyl ester

Guidance literature:: C₅₂H₇₁NO₁₀SSi₂; With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With methyl trifluoromethanesulfonate; In dichloromethane; at 40 ℃; for 48h;

With trifluoroacetic acid; In chloroform; at 0 ℃; for 0.5h;
DOI:10.1039/c3ob41212a

Reference yield:

: 69304-37-6
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

: 1451369-70-2
N-tertbutyloxycarbonyl-trans-4-O-(3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl)oxy-L-proline benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine / 5 h / 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 h / 0 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 16 h / 20 °C / Molecular sieve; Inert atmosphere

4.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

4.2: 48 h / 40 °C

4.3: 0.5 h / 0 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1039/c3ob41212a

Reference yield:

: 1451369-72-4
4-methylphenyl 3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-L-arabinofuranoside

: 1451369-70-2
N-tertbutyloxycarbonyl-trans-4-O-(3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl)oxy-L-proline benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 h / 0 °C

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 16 h / 20 °C / Molecular sieve; Inert atmosphere

3.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 48 h / 40 °C

3.3: 0.5 h / 0 °C

With 2,6-di-tert-butyl-4-methylpyridine; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1039/c3ob41212a