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

Base Information

Chemical Name:((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane
CAS No.:170706-53-3
Molecular Formula:C₂₉H₄₂O₄Si
Molecular Weight:482.736
Hs Code.:

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

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Chemical Property of ((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Technology Process of ((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

There total 2 articles about ((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 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: 90.0%

: 100-39-0
benzyl bromide

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

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

Guidance literature:: With potassium hydride; In tetrahydrofuran; at 45 ℃; for 1h;
DOI:10.1021/ja00146a008

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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With camphor-10-sulfonic acid; potassium hydride; In tetrahydrofuran; methanol;
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

: 3-((2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-6-benzyloxymethyl-3-hydroxy-4a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl)-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 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

2: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

3: 90 percent / benzene / 1 h / 50 °C

4: 96 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

5: 92 percent / (-)-diethyl tartrate, Ti(O-i-Pr)4, tert-BuOOH / CH₂Cl₂ / 14 h / -25 °C

6: 94 percent / SO₃*pyridine, Et₃N / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

7: 90 percent / PhCO₂H / benzene / 0.5 h / 25 °C

8: 96 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C

9: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 13 h / 0 °C

10: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 48 h / 25 °C

11: 91 percent / KH / tetrahydrofuran / 0.25 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; benzene;
DOI:10.1021/ja00146a008