[(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-yl]-methanol

Base Information

Chemical Name:[(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-yl]-methanol
CAS No.:250226-88-1
Molecular Formula:C₃₀H₄₆O₇Si
Molecular Weight:546.777
Hs Code.:

Synonyms:[(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of [(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-yl]-methanol

There total 12 articles about [(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-yl]-methanol 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:

: (2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2-methoxymethoxy-ethyl)-tetrahydro-pyran

: 250226-88-1
[(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With camphor-10-sulfonic acid; In methanol; dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(02)00045-5

Reference yield:

: 81972-20-5
2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol

: 250226-88-1
[(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

2: hydrogen / Pd(OH)2/C / ethyl acetate; methanol / 20 °C

3: CSA / dimethylformamide; CH₂Cl₂ / 20 °C

4: NaHMDS; Bu₄NI / dimethylformamide / 0 °C

5: CSA; MeOH / CH₂Cl₂ / 20 °C

6: 2,6-lutidine / CH₂Cl₂ / 0 °C

7: DIBAL-H / CH₂Cl₂ / -78 °C

8: i-Pr₂NEt; Bu₄NI / CH₂Cl₂ / 0 °C

9: CSA; MeOH / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; methanol; dmap; camphor-10-sulfonic acid; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol990885n

Reference yield:

: 82614-10-6
ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate

: 250226-88-1
[(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2: 100 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

3: hydrogen / Pd(OH)2/C / ethyl acetate; methanol / 20 °C

4: CSA / dimethylformamide; CH₂Cl₂ / 20 °C

5: NaHMDS; Bu₄NI / dimethylformamide / 0 °C

6: CSA; MeOH / CH₂Cl₂ / 20 °C

7: 2,6-lutidine / CH₂Cl₂ / 0 °C

8: DIBAL-H / CH₂Cl₂ / -78 °C

9: i-Pr₂NEt; Bu₄NI / CH₂Cl₂ / 0 °C

10: CSA; MeOH / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; methanol; dmap; camphor-10-sulfonic acid; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol990885n