2-(trimethylsilyl)ethyl 4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
CAS No.:174149-13-4
Molecular Formula:C₂₈H₄₄O₇Si₂
Molecular Weight:548.824
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

There total 10 articles about 2-(trimethylsilyl)ethyl 4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 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: 98.0%

: 174149-12-3
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

: 174149-13-4
2-(trimethylsilyl)ethyl 4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Guidance literature:: With hydrogen; acetic acid; palladium on activated charcoal; In methanol; at 50 ℃; for 24h;
DOI:10.1021/jo951067l

Reference yield:

: 81342-44-1
(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 174149-13-4
2-(trimethylsilyl)ethyl 4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: Amberlite IRA 910 / methanol / 2 h / 25 °C

2: 89 percent / PTSA / acetonitrile / 3 h / 25 °C

3: 1.) NaH / 1.) DMF, 20 deg C, 2 h, 2.) 25 deg C, 3 h

4: 0.5 M HCl / methanol / 2 h / Heating

5: imidazole / dimethylformamide / 5 h / 25 °C

6: DMSO/Ac₂O / 2 h / 65 °C

7: 72 percent / tetrahydrofuran / 2 h / -78 °C

8: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, -78 deg C, 2.) MeOH, - 78 deg C, 1 h

9: 98 percent / H₂, AcOH / Pd/C / methanol / 24 h / 50 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; Amberlite IRA 910; hydrogen; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo951067l

Reference yield:

: 81336-89-2,81336-96-1,117252-95-6,132871-94-4,117252-72-9
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triol

: 174149-13-4
2-(trimethylsilyl)ethyl 4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / PTSA / acetonitrile / 3 h / 25 °C

2: 1.) NaH / 1.) DMF, 20 deg C, 2 h, 2.) 25 deg C, 3 h

3: 0.5 M HCl / methanol / 2 h / Heating

4: imidazole / dimethylformamide / 5 h / 25 °C

5: DMSO/Ac₂O / 2 h / 65 °C

6: 72 percent / tetrahydrofuran / 2 h / -78 °C

7: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, -78 deg C, 2.) MeOH, - 78 deg C, 1 h

8: 98 percent / H₂, AcOH / Pd/C / methanol / 24 h / 50 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; hydrogen; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo951067l