(3aR,5S,6S,6aR)-6-Benzyloxy-5-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-vinyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5S,6S,6aR)-6-Benzyloxy-5-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-vinyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
CAS No.:208174-51-0
Molecular Formula:C₂₅H₄₂O₆Si₂
Molecular Weight:494.776
Hs Code.:

Synonyms:(3aR,5S,6S,6aR)-6-Benzyloxy-5-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-vinyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5S,6S,6aR)-6-Benzyloxy-5-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-vinyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

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Technology Process of (3aR,5S,6S,6aR)-6-Benzyloxy-5-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-vinyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 7 articles about (3aR,5S,6S,6aR)-6-Benzyloxy-5-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-vinyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 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: 90.0%

: 75-77-4
chloro-trimethyl-silane

: 106445-05-0
3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

: 208174-51-0
(3aR,5S,6S,6aR)-6-Benzyloxy-5-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-vinyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: With triethylamine; In N,N-dimethyl-formamide; at 70 ℃; for 48h;
DOI:10.1039/a800486b

Reference yield:

: 75-77-4
chloro-trimethyl-silane

: 106445-05-0
3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

: (3aR,5S,6S,6aR)-6-Benzyloxy-5-[(E)-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-vinyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

: 208174-51-0
(3aR,5S,6S,6aR)-6-Benzyloxy-5-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-vinyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1039/a800486b

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 208174-51-0
(3aR,5S,6S,6aR)-6-Benzyloxy-5-[(Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-vinyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

2: (COCl)2, DMSO

3: LDA / tetrahydrofuran / -78 - 20 °C

With dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1039/a800486b