1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne

Base Information

Chemical Name:1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne
CAS No.:221044-97-9
Molecular Formula:C₂₆H₄₀O₆Si
Molecular Weight:476.686
Hs Code.:

Synonyms:1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne

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Chemical Property of 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne

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Technology Process of 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne

There total 5 articles about 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne 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: 65.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 221044-89-9
1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne

: 221044-97-9
1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne

: (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-{(4R,5S)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-2-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,2-dimethyl-[1,3]dioxane

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; Yields of byproduct given;
DOI:10.1039/a808848i

Reference yield: 65.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 221044-89-9
1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne

: 221044-97-9
1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne

: (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-{(4R,5S)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-2-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,2-dimethyl-[1,3]dioxane

: (R)-1-{(4R,5R)-5-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-phenyl-prop-2-yn-1-ol

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1016/S0957-4166(03)00532-9

Reference yield:

: 357604-61-6
2,3:4,6-di-O-isopropylidene-D-mannopyranose

: 221044-97-9
1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne

Guidance literature:: Multi-step reaction with 2 steps

1.1: BuLi / tetrahydrofuran; hexane / -78 °C

1.2: 57 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 65 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / 20 °C

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/S0957-4166(03)00532-9