(2R,3S,5R,6S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

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Chemical Name:(2R,3S,5R,6S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran
CAS No.:632354-61-1
Molecular Formula:C₃₄H₅₂O₄Si₂
Molecular Weight:580.955
Hs Code.:

Synonyms:(2R,3S,5R,6S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

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Chemical Property of (2R,3S,5R,6S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

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Technology Process of (2R,3S,5R,6S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

There total 9 articles about (2R,3S,5R,6S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran 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: 95.0%

: 1066-54-2
trimethylsilylacetylene

: 632354-32-6
trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-2-ylmethyl ester

: 632354-61-1
(2R,3S,5R,6S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;
DOI:10.1021/jo035145d

Reference yield:

: 100-39-0
benzyl bromide

: 632354-61-1
(2R,3S,5R,6S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

2: 100 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

3: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

4: 1.84 g / 2,6-lutidine / CH₂Cl₂ / 0.75 h

5: 95 percent / n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jo035145d

Reference yield:

: (2S,3R)-2-(2-benzyloxyethyl)-2-methyl-3-(toluene-4-sulfonyl)oxirane

: 632354-61-1
(2R,3S,5R,6S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 8 steps

1: 81 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.5 h / -100 °C

2: 93 percent / TsOH*H₂O / CH₂Cl₂ / 23 h / 0 °C

3: 99 percent / NaBH₄ / methanol; CH₂Cl₂ / 1 h / -78 °C

4: 100 percent / KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

5: 100 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

6: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

7: 1.84 g / 2,6-lutidine / CH₂Cl₂ / 0.75 h

8: 95 percent / n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; toluene;
DOI:10.1021/jo035145d