1-[(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-one

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Chemical Name:1-[(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-one
CAS No.:455958-53-9
Molecular Formula:C₃₂H₅₀O₈Si
Molecular Weight:590.83
Hs Code.:

1-[(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-one

Synonyms:1-[(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-one

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Chemical Property of 1-[(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-one

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Technology Process of 1-[(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-one

There total 13 articles about 1-[(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-one 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: 100.0%

: 455958-51-7
1-[(2S,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

: 455958-53-9
1-[(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/ol026261q

Reference yield:

: C₁₅H₂₀O₅

: 455958-53-9
1-[(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 94 percent / CSA / dimethylformamide / 20 °C

2.1: 99 percent / H₂ / Pd(OH)2 / ethyl acetate / 20 °C

3.1: NaH / tetrahydrofuran / 20 °C

4.1: CSA; methanol / 20 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

6.1: CSA; methanol / 20 °C

7.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

8.1: t-butyllithium / tetrahydrofuran; pentane; hexamethylphosphoric acid triamide / 0.17 h / -78 °C

8.2: 76 percent / tetrahydrofuran; pentane; hexamethylphosphoric acid triamide / 0.25 h / -78 °C

9.1: 100 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; methanol; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; tert.-butyl lithium; sodium hydride; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; pentane; 9.1: Swern oxidation;
DOI:10.1021/ol026261q

Reference yield:

: 455958-46-0
C₁₈H₂₄O₅

: 455958-53-9
1-[(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-4-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / H₂ / Pd(OH)2 / ethyl acetate / 20 °C

2.1: NaH / tetrahydrofuran / 20 °C

3.1: CSA; methanol / 20 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

5.1: CSA; methanol / 20 °C

6.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

7.1: t-butyllithium / tetrahydrofuran; pentane; hexamethylphosphoric acid triamide / 0.17 h / -78 °C

7.2: 76 percent / tetrahydrofuran; pentane; hexamethylphosphoric acid triamide / 0.25 h / -78 °C

8.1: 100 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; methanol; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; tert.-butyl lithium; sodium hydride; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; pentane; 8.1: Swern oxidation;
DOI:10.1021/ol026261q