2-O-benzoyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose

Base Information

Chemical Name:2-O-benzoyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose
CAS No.:1268604-22-3
Molecular Formula:C₅₈H₇₈O₁₅Si₂
Molecular Weight:1071.42
Hs Code.:

2-O-benzoyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose

Synonyms:2-O-benzoyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose

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Chemical Property of 2-O-benzoyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose

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Technology Process of 2-O-benzoyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose

There total 7 articles about 2-O-benzoyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose 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: 93.0%

: 1268604-21-2
2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose

: 204918-58-1
p-cresyl-2-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-D-arabinofuranoside

: 1268604-22-3
2-O-benzoyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose

Guidance literature:: With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h; stereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1021/ja109932t

Reference yield:

: 917590-92-2
p-tolyl 5-O-t-butyldiphenylsilyl-2,3-di-O-acetyl-1-thio-α-D-arabinofuranoside

: 1268604-22-3
2-O-benzoyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 2 h / 0 °C / Molecular sieve; Inert atmosphere

2.1: methanol; sodium methylate / 1 h / 0 - 20 °C / Inert atmosphere

2.2: Amberlyst H⁺ resin / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

5.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 2 h / 0 °C / Molecular sieve; Inert atmosphere

With methanol; N-iodo-succinimide; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja109932t

Reference yield:

: C₄₀H₅₀O₁₁Si

: 1268604-22-3
2-O-benzoyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: methanol; sodium methylate / 1 h / 0 - 20 °C / Inert atmosphere

1.2: Amberlyst H⁺ resin / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

4.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 2 h / 0 °C / Molecular sieve; Inert atmosphere

With methanol; N-iodo-succinimide; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja109932t