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

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
CAS No.:174149-12-3
Molecular Formula:C₄₂H₅₆O₇Si₂
Molecular Weight:729.073
Hs Code.:

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

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Chemical Property of 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-(hydroxymethyl)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

There total 8 articles about 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-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:

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

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

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; Amberlite IRA 910; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 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

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

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

: 117253-04-0
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

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

Guidance literature:: Multi-step reaction with 5 steps

1: 0.5 M HCl / methanol / 2 h / Heating

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

3: DMSO/Ac₂O / 2 h / 65 °C

4: 72 percent / tetrahydrofuran / 2 h / -78 °C

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

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; acetic anhydride; ozone; dimethyl sulfoxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo951067l