[(1R,2R)-2-Benzyloxymethoxymethyl-1-ethyl-3-(tetrahydro-pyran-2-yloxy)-propoxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(1R,2R)-2-Benzyloxymethoxymethyl-1-ethyl-3-(tetrahydro-pyran-2-yloxy)-propoxy]-tert-butyl-dimethyl-silane
• CAS No.: 133377-99-8
• Molecular Formula: C₂₅H₄₄O₅Si
• Molecular Weight: 452.707

Synonyms:[(1R,2R)-2-Benzyloxymethoxymethyl-1-ethyl-3-(tetrahydro-pyran-2-yloxy)-propoxy]-tert-butyl-dimethyl-silane

Chemical Property of [(1R,2R)-2-Benzyloxymethoxymethyl-1-ethyl-3-(tetrahydro-pyran-2-yloxy)-propoxy]-tert-butyl-dimethyl-silane

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Technology Process of [(1R,2R)-2-Benzyloxymethoxymethyl-1-ethyl-3-(tetrahydro-pyran-2-yloxy)-propoxy]-tert-butyl-dimethyl-silane

There total 8 articles about [(1R,2R)-2-Benzyloxymethoxymethyl-1-ethyl-3-(tetrahydro-pyran-2-yloxy)-propoxy]-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: 94.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2R,3R)-2-Benzyloxymethoxymethyl-1-(tetrahydro-pyran-2-yloxy)-pentan-3-ol → [(1R,2R)-2-Benzyloxymethoxymethyl-1-ethyl-3-(tetrahydro-pyran-2-yloxy)-propoxy]-tert-butyl-dimethyl-silane (133377-99-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;

DOI:10.1016/0040-4039(91)80872-4

Reference yield: 91.0%

3,4-dihydro-2H-pyran (110-87-2) + (2S,3R)-2-Benzyloxymethoxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-pentan-1-ol → [(1R,2R)-2-Benzyloxymethoxymethyl-1-ethyl-3-(tetrahydro-pyran-2-yloxy)-propoxy]-tert-butyl-dimethyl-silane (133377-99-8)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 7h; Ambient temperature;

DOI:10.1016/0040-4039(91)80872-4

Reference yield:

(R)-2-Benzyloxymethoxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde (133377-92-1) → [(1R,2R)-2-Benzyloxymethoxymethyl-1-ethyl-3-(tetrahydro-pyran-2-yloxy)-propoxy]-tert-butyl-dimethyl-silane (133377-99-8)

Guidance literature:

Multi-step reaction with 4 steps

1: diethyl ether / -78 °C / other alkyl-metal compounds: diastereoselectivity

2: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

3: 64 percent / pyridinium p-toluenesulfonate / ethanol / 72 h / Ambient temperature

4: 91 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 7 h / Ambient temperature

With 2,6-dimethylpyridine; pyridinium p-toluenesulfonate; In diethyl ether; ethanol; dichloromethane;

DOI:10.1016/0040-4039(91)80872-4

upstream raw materials:

3,4-dihydro-2H-pyran

t-butyldimethylsiyl triflate

(2S,3R)-2-Benzyloxymethoxymethyl-pentane-1,3-diol

[(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pentyloxymethoxymethyl]-benzene

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