methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside

Base Information

Chemical Name:methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside
CAS No.:402758-94-5
Molecular Formula:C₄₈H₅₆O₉Si
Molecular Weight:805.053
Hs Code.:

Synonyms:methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside

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Chemical Property of methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside

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Technology Process of methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside

There total 9 articles about methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-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: 68.0%

: 402758-93-4
methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-arabinofuranoside

: 402758-94-5
methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 2h;
DOI:10.1021/jo010910e

Reference yield:

: 100-39-0
benzyl bromide

: 402758-94-5
methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: NaH / dimethylformamide / 2 h / 0 °C

2: 580 mg / n-Bu₄NF / tetrahydrofuran / 20 °C

3: 76 percent / pyridine / 24 h / 20 °C

4: 60 percent / molecular sieves; NIS; AgOTf / CH₂Cl₂ / 0 °C

5: 68 percent / NaOCH₃ / methanol / 2 h / 20 °C

With N-iodo-succinimide; molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Zemplen deacylation;
DOI:10.1021/jo010910e

Reference yield:

: 164454-52-8
methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside

: 402758-94-5
methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: NaH / dimethylformamide / 2 h / 0 °C

2: 580 mg / n-Bu₄NF / tetrahydrofuran / 20 °C

3: 76 percent / pyridine / 24 h / 20 °C

4: 60 percent / molecular sieves; NIS; AgOTf / CH₂Cl₂ / 0 °C

5: 68 percent / NaOCH₃ / methanol / 2 h / 20 °C

With N-iodo-succinimide; molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Zemplen deacylation;
DOI:10.1021/jo010910e