5-Benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-β-D-ribose

Base Information

Chemical Name:5-Benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-β-D-ribose
CAS No.:1583259-73-7
Molecular Formula:C₂₈H₃₄O₅Si
Molecular Weight:478.66
Hs Code.:

Synonyms:

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Chemical Property of 5-Benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-β-D-ribose

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Technology Process of 5-Benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-β-D-ribose

There total 9 articles about 5-Benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-β-D-ribose 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:

: C₃₁H₄₀O₆Si

: 1583259-73-7
5-Benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-β-D-ribose

: 1583259-72-6
5-benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-α-D-ribose

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 2.5h; Overall yield = 87.2 mg; diastereoselective reaction;
DOI:10.1021/ja502205q

Reference yield:

: 4799-68-2
3-benzyloxypropan-1-ol

: 1583259-73-7
5-Benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-β-D-ribose

: 1583259-72-6
5-benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-α-D-ribose

Guidance literature:: Multi-step reaction with 5 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 20 °C

2: copper dichloride; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid / ethyl acetate / 24 h / -30 °C / Molecular sieve

3: titanium(IV) dichlorodiisopropylate / dichloromethane / 16 h / -20 °C / Inert atmosphere

4: zinc; water; trifluoroacetic acid / toluene / 72 h / 20 °C

5: diisobutylaluminium hydride / toluene / 2 h / -78 °C

With titanium(IV) dichlorodiisopropylate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; water; diisobutylaluminium hydride; trifluoroacetic acid; copper dichloride; zinc; In dichloromethane; ethyl acetate; toluene; 3: |Mukaiyama Aldol Addition;
DOI:10.1021/ja502205q

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 1583259-73-7
5-Benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-β-D-ribose

: 1583259-72-6
5-benzyloxy-2-(tert-butyldiphenylsilyl)oxy-1-hydroxy-3-hydroxy-α-D-ribose

Guidance literature:: Multi-step reaction with 4 steps

1: copper dichloride; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid / ethyl acetate / 24 h / -30 °C / Molecular sieve

2: titanium(IV) dichlorodiisopropylate / dichloromethane / 16 h / -20 °C / Inert atmosphere

3: zinc; water; trifluoroacetic acid / toluene / 72 h / 20 °C

4: diisobutylaluminium hydride / toluene / 2 h / -78 °C

With titanium(IV) dichlorodiisopropylate; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; water; diisobutylaluminium hydride; trifluoroacetic acid; copper dichloride; zinc; In dichloromethane; ethyl acetate; toluene; 2: |Mukaiyama Aldol Addition;
DOI:10.1021/ja502205q