(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

Base Information

Chemical Name:(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
CAS No.:170706-74-8
Molecular Formula:C₃₆H₆₀O₅Si₂
Molecular Weight:629.04
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 170706-73-7
(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-hydroxymethyl-2,6-dimethyl-tetrahydro-pyran-3-ol

: 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

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 45 ℃; for 14h;
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

: 170706-74-8
(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

Guidance literature:: Multi-step reaction with 5 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

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

: 170706-74-8
(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

Guidance literature:: Multi-step reaction with 5 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

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