((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Base Information

Chemical Name:((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane
CAS No.:511511-36-7
Molecular Formula:C₂₄H₄₀O₅Si
Molecular Weight:436.664
Hs Code.:

Synonyms:((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Chemical Property of ((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Technology Process of ((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

There total 1 articles about ((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-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: 93.0%

: 511511-35-6
(2S,3S,4R,5R,6R)-2-Allyl-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxymethyl-tetrahydro-pyran-3-ol

: 74-88-4
methyl iodide

: 511511-36-7
((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

: 511511-36-7
((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

: [(2S,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Guidance literature:: ((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane; With ozone; In methanol; dichloromethane; at -70 ℃; for 2h;

With dimethylsulfide; In methanol; dichloromethane; at -50 - 20 ℃; for 16h; Further stages.;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

: 511511-36-7
((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

: (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: O₃ / CH₂Cl₂; methanol / 2 h / -70 °C

1.2: dimethyl sulfide / methanol; CH₂Cl₂ / 16 h / -50 - 20 °C

2.1: 0.952 g / LiAlH₄ / tetrahydrofuran / 0.5 h

3.1: pyridine / CH₂Cl₂ / 16 h

4.1: NaN₃ / dimethylformamide / 3 h / 60 °C

5.1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h

6.1: 88 percent / N-iodosuccinimide; mol. sieves 4 Angstroem; TfOH / toluene; dioxane; CH₂Cl₂ / 0.5 h / -20 °C

7.1: KOtBu / methanol; dioxane / 3 h

8.1: pTsOH / dimethylformamide / 1 h

9.1: NaH / dimethylformamide / 0.5 h / 0 °C

10.1: AcOH / H₂O / 1 h / 60 °C

11.1: potassium bromide; tetrabutylammonium chloride; NaHCO₃ / NaOCl; 2,2,6,6-tetramethylpiperidin-1-oxyl / CH₂Cl₂; H₂O / 1 h / 0 °C

With pyridine; N-iodo-succinimide; lithium aluminium tetrahydride; sodium azide; trifluorormethanesulfonic acid; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 7.1: Zemplen deacetylation;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2