4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-β-D-arabinofuranosyl]-α-D-arabinofuranoside

Base Information

Chemical Name:4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-β-D-arabinofuranosyl]-α-D-arabinofuranoside
CAS No.:1621691-81-3
Molecular Formula:C₄₈H₅₇ClO₁₃Si
Molecular Weight:905.511
Hs Code.:

Synonyms:4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-β-D-arabinofuranosyl]-α-D-arabinofuranoside

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Chemical Property of 4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-β-D-arabinofuranosyl]-α-D-arabinofuranoside

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Technology Process of 4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-β-D-arabinofuranosyl]-α-D-arabinofuranoside

There total 6 articles about 4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-β-D-arabinofuranosyl]-α-D-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:

: 1621691-61-9
phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside

: 1621691-68-6
4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-α-D-arabinofuranoside

: 1621691-82-4
4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-α-D-arabinofuranosyl]-α-D-arabinofuranoside

: 1621691-81-3
4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-β-D-arabinofuranosyl]-α-D-arabinofuranoside

Guidance literature:: phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside; 4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-α-D-arabinofuranoside; In dichloromethane; at 22 ℃; for 1h; Inert atmosphere; Molecular sieve;

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at -78 - 10 ℃; for 1h; Inert atmosphere; Molecular sieve;

With triethylamine; In methanol; dichloromethane; at 20 ℃; for 0.666667h; Overall yield = 80 %; stereoselective reaction;
DOI:10.1016/j.carres.2014.05.017

Reference yield:

: 1379681-43-2
phenyl 3,5-di-O-benzoyl-1-thio-α-D-arabinofuranoside

: 1621691-82-4
4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-α-D-arabinofuranosyl]-α-D-arabinofuranoside

: 1621691-81-3
4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-β-D-arabinofuranosyl]-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,4,6-trimethyl-pyridine / N,N-dimethyl-formamide / 1 h / 90 °C

2.1: sodium methylate / methanol / 48 h / 20 °C

2.2: Dowex 50Wx₄ (H⁺) ion-exchange resin

3.1: pyridine / dichloromethane / 1 h / 0 °C

4.1: sodium 2,2,2-trifluoroacetate / dichloromethane / 1 h / 0 °C

5.1: dichloromethane / 1 h / 22 °C / Inert atmosphere; Molecular sieve

5.2: 1 h / -78 - 10 °C / Inert atmosphere; Molecular sieve

5.3: 0.67 h / 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; sodium methylate; sodium 2,2,2-trifluoroacetate; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2014.05.017

Reference yield:

: 1621691-60-8
phenyl 5-O-benzoyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside

: 1621691-82-4
4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-α-D-arabinofuranosyl]-α-D-arabinofuranoside

: 1621691-81-3
4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-β-D-arabinofuranosyl]-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium 2,2,2-trifluoroacetate / dichloromethane / 1 h / 0 °C

2.1: dichloromethane / 1 h / 22 °C / Inert atmosphere; Molecular sieve

2.2: 1 h / -78 - 10 °C / Inert atmosphere; Molecular sieve

2.3: 0.67 h / 20 °C

With sodium 2,2,2-trifluoroacetate; In dichloromethane;
DOI:10.1016/j.carres.2014.05.017