5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran

Base Information

• Chemical Name: 5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran
• CAS No.: 912281-14-2
• Molecular Formula: C₃₇H₆₂O₇Si₂
• Molecular Weight: 675.066

Synonyms:5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran

Chemical Property of 5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran

There total 6 articles about 5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran 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: 84.0%

5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3-ol (912281-35-7) + p-methoxybenzyl chloride (824-94-2) → 5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran (912281-14-2)

Guidance literature:

With potassium hydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2006.07.027

Reference yield:

tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane (912281-33-5) → 5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran (912281-14-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: thexylborane / tetrahydrofuran / 0 °C

1.2: 89 percent / aq. NaOH; H₂O₂

2.1: 99 percent / imidazole / dimethylformamide / 0 °C

3.1: 100 percent / H₂ / Pd(OH)2/C / 20 °C

4.1: 84 percent / KH / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; thexylborane; hydrogen; potassium hydride; palladium dihydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.07.027

Reference yield:

2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol (912281-34-6) → 5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran (912281-14-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / imidazole / dimethylformamide / 0 °C

2: 100 percent / H₂ / Pd(OH)2/C / 20 °C

3: 84 percent / KH / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; hydrogen; potassium hydride; palladium dihydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.07.027

upstream raw materials:

5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3-ol

p-methoxybenzyl chloride

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

2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Downstream raw materials:

4-Bromo-benzoic acid (R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-2-hydroxy-propyl ester

(E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dienoic acid ethyl ester

(E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dien-1-ol

((2R,3R)-3-{1-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-vinyl}-2-methyl-oxiranyl)-methanol

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