2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside
CAS No.:115988-73-3
Molecular Formula:C₃₈H₅₆O₆Si₂
Molecular Weight:665.03
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside

There total 8 articles about 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside 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: 79.0%

: 117253-05-1
2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

: 18162-48-6
tert-butyldimethylsilyl chloride

: 115988-73-3
2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 48h;
DOI:10.1021/jo00259a006

Reference yield:

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 115988-73-3
2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / HgO, HgBr₂, CaSO₄ / CHCl₃ / 48 h / Ambient temperature

2: 90 percent / CH₃ONa / methanol / 3 h

3: 83 percent / p-TsOH*H₂O / tetrahydrofuran / 27 h / 22 °C

4: 4 percent / t-Bu₄NHSO₄, 1.3 M aq. NaOH / CH₂Cl₂ / 48 h / Heating

5: 79 percent / ethereal HCl, NaCNBH₃, molecular sieves 3A / tetrahydrofuran / 22 °C

6: 79 percent / imidazole / dimethylformamide / 48 h

With 1H-imidazole; hydrogenchloride; calcium sulfate; sodium hydroxide; 3 A molecular sieve; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; tetra-tert-butylammonium hydrogen sulfate; mercury dibromide; mercury(II) oxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo00259a006

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 115988-73-3
2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(dimethyl-tert-butylsilyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / p-TsOH*H₂O / tetrahydrofuran / 27 h / 22 °C

2: 4 percent / t-Bu₄NHSO₄, 1.3 M aq. NaOH / CH₂Cl₂ / 48 h / Heating

3: 79 percent / ethereal HCl, NaCNBH₃, molecular sieves 3A / tetrahydrofuran / 22 °C

4: 79 percent / imidazole / dimethylformamide / 48 h

With 1H-imidazole; hydrogenchloride; sodium hydroxide; 3 A molecular sieve; sodium cyanoborohydride; toluene-4-sulfonic acid; tetra-tert-butylammonium hydrogen sulfate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00259a006