2-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-ethanol

Base Information

Chemical Name:2-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-ethanol
CAS No.:170706-54-4
Molecular Formula:C₂₉H₄₄O₅Si
Molecular Weight:500.751
Hs Code.:

Synonyms:2-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-ethanol

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Chemical Property of 2-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-ethanol

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Technology Process of 2-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-ethanol

There total 3 articles about 2-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-ethanol 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:

: 131310-62-8
tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

: 170706-54-4
2-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / CSA / methanol / 1 h / 0 °C

2: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

3: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1.5 h, 2.) THF, 0 deg C, 1 h

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

Reference yield:

: 170706-52-2
(2R,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-methyl-6-vinyl-tetrahydro-pyran-3-ol

: 170706-54-4
2-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 2 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, 1.5 h, 2.) THF, 0 deg C, 1 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; potassium hydride; In tetrahydrofuran;
DOI:10.1021/ja00146a008

Reference yield:

: 170706-53-3
((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

: 170706-54-4
2-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-ethanol

Guidance literature:: With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; Yield given. Multistep reaction; 1.) THF, 25 deg C, 1.5 h, 2.) THF, 0 deg C, 1 h;
DOI:10.1021/ja00146a008