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

Base Information

Chemical Name:[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-methanol
CAS No.:170706-75-9
Molecular Formula:C₃₀H₄₆O₅Si
Molecular Weight:514.778
Hs Code.:

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

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

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

There total 7 articles about [(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-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: 89.0%

: 170706-74-8
(2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-tetrahydro-pyran

: 170706-75-9
[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With camphor-10-sulfonic acid; In methanol; at 0 ℃; for 1h;
DOI:10.1021/ja00146a008

Reference yield:

: 131311-02-9
(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 170706-75-9
[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

2: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1 h, 2.) THF, 0 deg C, 1 h

3: 88 percent / KH / tetrahydrofuran / 1 h / 45 °C

4: 89 percent / CSA / methanol / 1 h / 0 °C

5: 95 percent / imidazole / dimethylformamide / 14 h / 45 °C

6: 89 percent / CSA / methanol / 1 h / 0 °C

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; dihydrogen peroxide; potassium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00146a008

Reference yield:

: 100-39-0
benzyl bromide

: 170706-75-9
[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

2: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1 h, 2.) THF, 0 deg C, 1 h

3: 88 percent / KH / tetrahydrofuran / 1 h / 45 °C

4: 89 percent / CSA / methanol / 1 h / 0 °C

5: 95 percent / imidazole / dimethylformamide / 14 h / 45 °C

6: 89 percent / CSA / methanol / 1 h / 0 °C

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; dihydrogen peroxide; potassium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00146a008