5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-1a-(3-fluorophenyl)-2-methoxy-α-D-ribofuranose

Base Information

Chemical Name:5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-1a-(3-fluorophenyl)-2-methoxy-α-D-ribofuranose
CAS No.:1583260-16-5
Molecular Formula:C₂₅H₃₅FO₄Si
Molecular Weight:446.634
Hs Code.:

Synonyms:5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-1a-(3-fluorophenyl)-2-methoxy-α-D-ribofuranose

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-1a-(3-fluorophenyl)-2-methoxy-α-D-ribofuranose

Chemical Property:

Purity/Quality:: 97% ^*data from raw suppliers

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Technology Process of 5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-1a-(3-fluorophenyl)-2-methoxy-α-D-ribofuranose

There total 18 articles about 5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-1a-(3-fluorophenyl)-2-methoxy-α-D-ribofuranose 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: 97.0%

: 5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-(3-fluorophenyl)-2-methoxy-D-ribofuranose

: 1583260-16-5
5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-1a-(3-fluorophenyl)-2-methoxy-α-D-ribofuranose

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -40 ℃; for 2h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ja502205q

Reference yield:

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

: 1583260-16-5
5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-1a-(3-fluorophenyl)-2-methoxy-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 20 °C

2.1: 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

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

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

5.1: 2,6-dimethylpyridine / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; pentane / 1 h / -78 °C

6.2: 0.5 h

7.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 2 h / -40 °C / Inert atmosphere

With 2,6-dimethylpyridine; triethylsilane; n-butyllithium; titanium(IV) dichlorodiisopropylate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; water; trifluoroacetic acid; copper dichloride; zinc; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; pentane; 3.1: |Mukaiyama Aldol Addition;
DOI:10.1021/ja502205q

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 1583260-16-5
5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-1a-(3-fluorophenyl)-2-methoxy-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: 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

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

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

4.1: 2,6-dimethylpyridine / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; pentane / 1 h / -78 °C

5.2: 0.5 h

6.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 2 h / -40 °C / Inert atmosphere

With 2,6-dimethylpyridine; triethylsilane; n-butyllithium; titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; water; trifluoroacetic acid; copper dichloride; zinc; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; pentane; 2.1: |Mukaiyama Aldol Addition;
DOI:10.1021/ja502205q