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

Base Information

• Chemical Name: tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane
• CAS No.: 436153-69-4
• Molecular Formula: C₂₁H₃₂O₄Si
• Molecular Weight: 376.568

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,4aR,6S,7R,8aS)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (315203-85-1) → tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane (436153-69-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2018.01.039

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane (436153-69-4)

Guidance literature:

Multi-step reaction with 10 steps

1: Inert atmosphere

2: 10-camphorsufonic acid / Inert atmosphere

3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4: diisobutylaluminium hydride / Inert atmosphere

5: tert.-butylhydroperoxide; titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / Molecular sieve; Inert atmosphere

6: sulfur trioxide pyridine complex; triethylamine; dimethyl sulfoxide / Inert atmosphere

7: sodium hexamethyldisilazane / Inert atmosphere

8: tetrabutyl ammonium fluoride / Inert atmosphere

9: pyridinium p-toluenesulfonate / Inert atmosphere

10: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In N,N-dimethyl-formamide; 5: |Sharpless Asymmetric Epoxidation / 6: |Parikh-Doering Oxidation;

DOI:10.1016/j.tet.2018.01.039

Reference yield:

(2S,3R)-3-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl]-oxirane-2-carbaldehyde → tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane (436153-69-4)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hexamethyldisilazane / Inert atmosphere

2: tetrabutyl ammonium fluoride / Inert atmosphere

3: pyridinium p-toluenesulfonate / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2018.01.039

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,4aR,6S,7R,8aS)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

2-deoxy-D-ribose

((2R,3R)-3-(((2R,4S,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl)methyl)oxiran-2-yl)methanol

Downstream raw materials:

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

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

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

(4aR,5aS,6aR,8S,9R,11aS,12aR,13aS)-8-(3-Hydroxy-propyl)-2-(4-methoxy-phenyl)-8-methyl-dodecahydro-1,3,5,7,12-pentaoxa-cyclohepta[b]anthracen-9-ol

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