(3aS,6S,7S,7aS)-6-benzyloxy-2,2-dimethyl-7-(tert-butyldimethylsilyl)oxy-tetrahydro-1,3-dioxolo[4,5-c]pyran

Base Information

Chemical Name:(3aS,6S,7S,7aS)-6-benzyloxy-2,2-dimethyl-7-(tert-butyldimethylsilyl)oxy-tetrahydro-1,3-dioxolo[4,5-c]pyran
CAS No.:389086-19-5
Molecular Formula:C₂₁H₃₄O₅Si
Molecular Weight:394.583
Hs Code.:

Synonyms:(3aS,6S,7S,7aS)-6-benzyloxy-2,2-dimethyl-7-(tert-butyldimethylsilyl)oxy-tetrahydro-1,3-dioxolo[4,5-c]pyran

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Chemical Property of (3aS,6S,7S,7aS)-6-benzyloxy-2,2-dimethyl-7-(tert-butyldimethylsilyl)oxy-tetrahydro-1,3-dioxolo[4,5-c]pyran

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Technology Process of (3aS,6S,7S,7aS)-6-benzyloxy-2,2-dimethyl-7-(tert-butyldimethylsilyl)oxy-tetrahydro-1,3-dioxolo[4,5-c]pyran

There total 1 articles about (3aS,6S,7S,7aS)-6-benzyloxy-2,2-dimethyl-7-(tert-butyldimethylsilyl)oxy-tetrahydro-1,3-dioxolo[4,5-c]pyran 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%

: 26685-74-5
1-O-benzyl-3,4-O-isopropylidene-β-L-ribopyranose

: 18162-48-6
tert-butyldimethylsilyl chloride

: 389086-19-5
(3aS,6S,7S,7aS)-6-benzyloxy-2,2-dimethyl-7-(tert-butyldimethylsilyl)oxy-tetrahydro-1,3-dioxolo[4,5-c]pyran

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 16h;
DOI:10.1016/S0040-4020(02)01380-7

Reference yield:

: 389086-19-5
(3aS,6S,7S,7aS)-6-benzyloxy-2,2-dimethyl-7-(tert-butyldimethylsilyl)oxy-tetrahydro-1,3-dioxolo[4,5-c]pyran

: 389085-95-4
(4R,5R,6S,7S)-5-(tert-butyldimethylsilyl)oxy-8-(tert-butyldiphenylsilyl)oxy-5,6-(dimethylmethylenedioxy)-4-methylocten-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 83 percent / hydrogen / Pd(OH)2 / ethanol / 48 h

2.1: 90 percent / benzene / 39 h / Heating

3.1: 94 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

4.1: Mg / diethyl ether / 0.5 h / Heating

4.2: 94 percent / diethyl ether / 5 h / 0 °C

5.1: 54 percent / BF₃*Et₂O / tetrahydrofuran; diethyl ether / 1 h / -78 °C

With 1H-imidazole; boron trifluoride diethyl etherate; hydrogen; magnesium; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(02)01380-7

Reference yield:

: 389086-19-5
(3aS,6S,7S,7aS)-6-benzyloxy-2,2-dimethyl-7-(tert-butyldimethylsilyl)oxy-tetrahydro-1,3-dioxolo[4,5-c]pyran

: 389086-14-0
C₇₉H₁₃₀O₁₁S₂Si₄

Guidance literature:: Multi-step reaction with 6 steps

1.1: 83 percent / hydrogen / Pd(OH)2 / ethanol / 48 h

2.1: 90 percent / benzene / 39 h / Heating

3.1: 94 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

4.1: Mg / diethyl ether / 0.5 h / Heating

4.2: 94 percent / diethyl ether / 5 h / 0 °C

5.1: 54 percent / BF₃*Et₂O / tetrahydrofuran; diethyl ether / 1 h / -78 °C

6.1: BuLi; HMDS / hexane; tetrahydrofuran / 0.5 h / -78 °C

6.2: tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

With 1H-imidazole; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; magnesium; 1,1,1,3,3,3-hexamethyl-disilazane; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(02)01380-7