2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose

Base Information

Chemical Name:2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose
CAS No.:948036-11-1
Molecular Formula:C₃₅H₄₆O₆Si
Molecular Weight:590.832
Hs Code.:

Synonyms:2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose

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Chemical Property of 2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose

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Technology Process of 2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose

There total 8 articles about 2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose 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: 62.0%

: 948036-10-0
(3S,4R,5R,6R)-6-[(tert-butyldimethylsilyl)oxy]methyl-3,4,5-trisbenzyloxy-tetrahydropyran-2-one

: 3536-96-7
vinylmagnesium chloride

: 948036-11-1
2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose

Guidance literature:: With cerium(III) chloride; In toluene; at -78 ℃; for 1h;
DOI:10.1016/j.tetlet.2007.06.057

Reference yield:

: 948036-05-3
(2S,3S,4S,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-4-trifluoromethanesulfonyloxy-tetrahydro-4H-pyran

: 948036-11-1
2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: 62 percent / 18-crown-6 / toluene / 24 h / 30 °C / sonication

2.1: 95 percent / NaOMe / methanol / 20 °C

3.1: 96 percent / NaH / dimethylformamide / 0 - 20 °C

4.1: PdCl₂ / acetate buffer / 4 h / 30 °C / sonication

4.2: DMSO; Ac₂O / 20 °C

5.1: 62 percent / CeCl₃ / toluene / 1 h / -78 °C

With cerium(III) chloride; 18-crown-6 ether; sodium methylate; sodium hydride; palladium dichloride; In methanol; acetate buffer; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tetlet.2007.06.057

Reference yield:

: 948036-07-5
(2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol

: 948036-11-1
2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: 96 percent / NaH / dimethylformamide / 0 - 20 °C

2.1: PdCl₂ / acetate buffer / 4 h / 30 °C / sonication

2.2: DMSO; Ac₂O / 20 °C

3.1: 62 percent / CeCl₃ / toluene / 1 h / -78 °C

With cerium(III) chloride; sodium hydride; palladium dichloride; In acetate buffer; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tetlet.2007.06.057