1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-methylene-L-xylitol

Base Information

Chemical Name:1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-methylene-L-xylitol
CAS No.:207232-14-2
Molecular Formula:C₂₂H₂₈O₃Si
Molecular Weight:368.548
Hs Code.:

Synonyms:1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-methylene-L-xylitol

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Chemical Property of 1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-methylene-L-xylitol

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Technology Process of 1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-methylene-L-xylitol

There total 13 articles about 1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-methylene-L-xylitol 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: 66.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 207232-13-1
1,4-anhydro-3-deoxy-3-C-methylene-L-xylitol

: 207232-14-2
1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-methylene-L-xylitol

Guidance literature:: With 1H-imidazole; In tetrahydrofuran;
DOI:10.1016/S0960-894X(98)00122-X

Reference yield:

: 207232-10-8
methyl 2,5-di-O-benzyl-L-xylofuranoside

: 207232-14-2
1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-methylene-L-xylitol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 75 percent / 2 h / 20 °C

2.1: 96 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 3 h / 20 °C

3.1: 85 percent / NaOMe / methanol / 2 h / 0 °C

4.1: 80 percent / DMSO; Ac₂O / 9 h / 20 °C

5.1: t-amyl alcohol; NaH / tetrahydrofuran; hexane / 0.03 h / 20 °C

5.2: 92 percent / tetrahydrofuran / 0.5 h / 20 °C

6.1: 75 percent / BCl₃ / CH₂Cl₂ / 0.5 h / -78 °C

7.1: 66 percent / imidazole / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; triethylsilane; tert-Amyl alcohol; trimethylsilyl trifluoromethanesulfonate; sodium methylate; acetic anhydride; boron trichloride; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 5.2: Wittig reaction;
DOI:10.1016/S0968-0896(01)00266-8

Reference yield:

: 207232-12-0
1,4-anhydro-2,5-di-O-benzyl-3-deoxy-3-C-methylene-L-xylitol

: 207232-14-2
1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-methylene-L-xylitol

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / BCl₃ / CH₂Cl₂ / 0.5 h / -78 °C

2: 66 percent / imidazole / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; boron trichloride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(01)00266-8